Acrylonitrile derivative, liquid crystal composition, and liquid crystal display device

ABSTRACT

An acrylonitrile derivative expressed by the following general formula I, a composition comprising the derivative and having an improved viscosity and optical anisotropy, and a liquid crystal display device: ##STR1## wherein rings A 1  to A 3  represent phenylene, cyclohexylene, dioxane, or pyrimidine, R 1  represents cyano group, halogen atom, an alkyl group, or an alkoxy group, and R2 represents ##STR2##

TECHNICAL FIELD

The present invention relates to a novel liquid crystalline compound, aliquid crystal composition comprising the compound, and a liquid crystaldisplay device comprising the composition.

BACKGROUND ART

Display devices which employ properties such as optical anisotropy anddielectric anisotropy of liquid crystal materials are widely used forwatches, desktop calculators, and others. As liquid crystal phase,nematic liquid crystal phase, smectic liquid crystal phase, andcholesteric liquid crystal phase are known, and nematic phase is mostgeneral for practical purposes. As the display mode in this case, thereexist TN (twisted nematic) mode, DS (dynamic scattering) mode, guesthost mode, and DAP (deformation of aligned phases) mode. Whereas manycompounds used for these types have heretofore been developed, there isno case in which a single compound is filled as it is in a displaydevice and actually used. As liquid crystal materials used for displaydevices, it is necessary that the materials exhibit a liquid crystalphase at a wide temperature range with room temperature being itscenter, are stable against moisture, light, heat, air, electric field,and electromagnetic radiation under the atmosphere in which thematerials are used, and have physical properties sufficient to drivedisplay devices. However, these requirements can not be satisfied with asingle compound. Then, a method has been adopted in which several kindof liquid crystalline compounds and furthermore non liquid-crystallinecompounds are mixed to prepare a composition which meets therequirements, and then supplied for actual uses. Physical propertiessuch as optical anisotropy, dielectric anisotropy, and electricalconductivity required of liquid crystal compositions depends on displaymode and shape of devices. In STN mode which is used particularly inrecent years for displays of liquid crystal display devices of a highquality, the ratio of elastic constants (k₃₃ /k₁₁) of liquid crystalcompositions must be enhanced to obtain a good display having a highsteepness. Then, compounds which have a high elastic constant, widerange of liquid crystal temperature, and high miscibility with otherliquid crystals, are stable, and have a low viscosity not to lose a highresponse speed have become an important question.

As examples of compounds having a high ratio of elastic constants,alkenyl compounds (Laid-open Japanese Patent Publication No. Sho59-176,221) expressed by formula (1) are widely known. However, sincethe temperature range of nematic liquid crystal of the compounds isnarrow, compounds having a high clearing point must be further added sothat the narrow temperature range of nematic liquid crystal can becompensated when the compounds of formula (1) are mixed with acomposition. However, since the compounds having a high clearing pointgenerally exhibit a high viscosity, addition of the compounds increasesviscosity of the whole of composition as the result. Derivatives ofcynnamonitrile (Laid-open Japanese Patent Publication No. Sho 55-9,012)expressed by formula (2) are also known as liquid crystalline compound.However, since the compounds are chemically unstable, they can hardly besaid to be ones of practical use. Whereas cyanocyclohexane derivativesin which cyano group substituted directly in cyclohexane ring (Journalof Molecular Crystal Liquid Crystal, No. 111, page 329, 1984) and whichare expressed by formula (3) are also known, the compounds have a highviscosity and a narrow temperature range of liquid crystal. Further, newcompounds such as difluorovinyl derivatives (Laid-open Japanese PatentPublication No. Hei 1-175,947) expressed by formula (4) and halogenizedvinyl derivatives (WO 93/07,234) expressed by formula (5) have beendeveloped. Whereas the former have a low viscosity, they are poor inreliability and have only a narrow liquid crystal range. The latter havea medium extent of the range of liquid crystal, but they are also poorin reliability and thus they have no practical uses. Then, discovery anddevelopment of new materials exhibiting a large elastic constants, andhaving a high clearing point, low viscosity, and high reliability havebeen expected. ##STR3##

DISCLOSURE OF THE INVENTION

An object of the present invention is to solve the disadvantages in theprior art described above. Another object of the present invention is toprovide novel crystalline compounds which maintain excellent propertiesas liquid crystal component, that is, a wide range of liquid crystaltemperature, good miscibility with other liquid crystals, and lowviscosity, and can impart large elastic constants to liquid crystals;compositions comprising the liquid crystalline compounds; and liquidcrystal display devices comprising the composition.

In order to achieve the objects described above, the present inventionhas the following aspects:

(1) An acrylonitrile derivative expressed by general formula I ##STR4##wherein ring A¹, ring A², and Ring A³ independently represent1,4-phenylene one or two hydrogen atoms of which may be replaced byfluorine atom, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, or1,3-pyrimidine-2,5-diyl, R¹ represents cyano group, halogen atom, analkyl group, an alkoxy group, an alkyl group one or more hydrogen atomsof which are replaced by fluorine atom, an alkoxy group one or morehydrogen atoms of which are replaced by fluorine atom, or an alkoxyalkylgroup when the ring A¹ represents 1,4-phenylene, but when the ring A¹represents 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, or1,3-pyrimidine-2,5-diyl, R¹ represents an alkyl group, an alkoxy group,or an alkoxyalkyl group, B¹, B², and B³ represent a covalent bond,ethylene, ethenylene, ethynylene, oxymethylene, carbonyloxy,1,4-butanediyl, or 1,4-butenediyl, n1, n2, and n3 are independently 0 or1, R² represents a group expressed by formula II or formula III ##STR5##wherein X represents hydrogen atom or fluorine atom, and ring Hrepresents 1,4-cyclohexylene, provided that in no case two or morehetero-rings are included in a molecule at the same time.

(2) The acrylonitrile derivative recited in (1) above wherein n1 and n2are 0.

(3) The acrylonitrile derivative recited in (1) above wherein n1 is 0and n2 is 1.

(4) The acrylonitrile derivative recited in (1) above wherein n1 and n2are 1.

(5) The acrylonitrile derivative recited in (1) above wherein R¹ is analkyl group, an alkoxy group, or an alkoxyalkyl group, ring A¹, ring A²,and ring A³ represent 1,4-phenylene one or two hydrogen atoms of whichmay be replaced by fluorine atom, or 1,4-cyclohexylene.

(6) The acrylonitrile derivative recited in (2) above wherein R¹represents an alkyl group, an alkoxy group, or an alkoxyalkyl group, andring A¹ represents 1,4-phenylene or 1,4-cyclohexylene.

(7) The acrylonitrile derivative recited in (5) above wherein either n1or n2 is 0, and both B² and B³ represent a covalent bond.

(8) The acrylonitrile derivative recited in (5) above wherein either n1or n2 is 0, B² and B³ independently represent a covalent bond or1,2-ethylene, and R² represents a group expressed by the formula II.

(9) The acrylonitrile derivative recited in (5) above wherein either n1or n2 is 0, B² and B³ independently represent a covalent bond or1,2-ethylene, and R² represents a group expressed by the formula III.

(10) The acrylonitrile derivative recited in (1) above wherein ring A¹represents 1,4-phenylene one or two hydrogen atoms of which may bereplaced by fluorine atom, and R¹ represents cyano group, halogen atom,an alkyl group one or more hydrogen atoms of which are replaced byfluorine atom, or an alkoxy group one or more hydrogen atoms of whichare replaced by fluorine atom.

(11) The acrylonitrile derivative recited in (2) above wherein ring A¹represents 1,4-phenylene one or more hydrogen atoms of which may bereplaced by fluorine atom, and R¹ represents cyano group, halogen atom,an alkyl group one or more hydrogen atoms of which are replaced byfluorine atom, or an alkoxy group one or more hydrogen atoms of whichare replaced by fluorine atom.

(12) The acrylonitrile derivative recited in (3) above wherein ring A¹represents 1,4-phenylene one or more hydrogen atoms may be replaced byfluorine atom, and R¹ represents cyano group, halogen atom, an alkylgroup one or more hydrogen atoms of which are replaced by fluorine atom,or an alkoxy group one or more hydrogen atoms of which are replaced byfluorine atom.

(13) The acrylonitrile derivative recited in (10) above wherein R¹represents cyano group or halogen atom.

(14) The acrylonitrile derivative recited in (10) above wherein eithern1 or n2 is 0, and both B² and B³ represent a covalent bond.

(15) The acrylonitrile derivative recited in (13) wherein either n1 orn2 is 0, B² and B³ represent a covalent bond, and R² represents a groupexpressed by the formula II.

(16) The acrylonitrile derivative recited in (13) above wherein eithern1 or n2 is 0, both B² and B³ represent a covalent bond, and R²represents a group expressed by the formula III.

(17) A liquid crystal composition comprising two or more components atleast one of which is a liquid crystalline compound expressed by thegeneral formula I.

(18) A liquid crystal composition comprising as a first component, atleast one acrylonitrile derivative recited in any one of aspects (1) to(16), and comprising as a second component, at least one compoundselected from the group consisting of the compounds expressed by any oneof the general formulas IV, V, and VI ##STR6## wherein R³ represents analkyl group having 1 to 10 carbon atoms, Y represents fluorine atom orchlorine atom, Q¹ and Q² independently represent hydrogen atom orfluorine atom, m is 1 or 2, and Z¹ and Z² independently represent --CH₂CH₂ -- or a covalent bond.

(19) A liquid crystal composition comprising as a first component, atleast one acrylonitrile derivative recited in any one of aspects (1) to(16), and comprising as a second component, at least one compoundselected from the group consisting of the compounds expressed by any oneof the general formula VII, VIII, IX, X, and XI ##STR7## wherein R⁴represents an alkyl group having 1 to 10 carbon atoms or an alkenylgroup having 2 to 10 carbon atoms, any methylene group (--CH₂ --) ineach of the alkyl group and alkenyl group may be replaced by oxygen atom(--O--), but in no case two or more methylene groups are continuouslyreplaced by oxygen group, Z³ represents --CH₂ CH₂ --, --COO--, or acovalent bond, Q³ represents hydrogen atom or fluorine atom, ring Crepresents 1,4-cyclohexylene, 1,4-phenylene, or 1,3-dioxane-2,5-diyl,and l is 0 or 1, ##STR8## wherein R⁵ represents an alkyl group having 1to 10 carbon atoms, Q⁴ represents hydrogen atom or fluorine atom, and ois 0 or 1, ##STR9## wherein R⁶ represents an alkyl group having 1 to 10carbon atoms, ring D represents 1,4-cyclohexylene or 1,4-phenylene, Q⁵and Q⁶ represent hydrogen atom or fluorine atom, respectively, Z⁴represents --COO-- or a covalent bond, and p is 0 or 1, ##STR10##wherein R⁷ and R⁸ independently represent an alkyl group having 1 to 10carbon atoms or an alkenyl group having 2 to 10 carbon atoms, anymethylene group (--CH₂ --) in each of the alkyl group and alkenyl groupmay be replaced by oxygen atom, but in no case two or more methylenegroups are continuously replaced by oxygen atom, ring E represents1,4-cyclohexylene, 1,3-pyrimidine-2,5-diyl, or 1,4-phenylene, ring Frepresents 1,4-cyclohexylene or 1,4-phenylene, and Z⁵ represents--C.tbd.C--, --COO--, --CH₂ CH₂ --, or a covalent bond ##STR11## whereinR⁹ represents an alkyl group or an alkoxy group having 1 to 10 carbonatoms, R¹⁰ represents an alkyl, an alkoxy, or an alkoxymethyl grouphaving 1 to 10 carbon atoms, ring G represents 1,4-cyclohexylene or1,3-pyrimidine-2,5-diyl, ring I and ring J independently represent1,4-cyclohexylene or 1,4-phenylene, Z⁶ represents --COO--, --CH₂ CH₂ --,or a covalent bond, Z⁷ represents --C.tbd.C--, --COO--, or a covalentbond, and Q⁷ represents hydrogen atom or fluorine atom.

(20) A liquid crystal composition comprising as a first component, atleast one liquid crystalline compound recited in any one of aspects (1)to (16), comprising, as a part of a second component, at least onecompound selected from the group consisting of the compounds expressedby any one of the general formulas IV, V, and VI, and comprising asother part of the second component, at least one compound selected fromthe group consisting of the compounds expressed by any one of thegeneral formulas VII, VIII, IX, X, and XI.

(21) A liquid crystal display device comprising a liquid crystalcomposition recited in any one of aspects (17) to (20).

BEST MODE FOR CARRYING OUT THE INVENTION

Acrylonitrile derivatives of the present invention, expressed by generalformula I, can also be expressed by any one of formulas XVII to XXIVwhen attention is paid to molecular terminal. ##STR12##

Among these, compounds having cyanoethylene group at a molecularterminal and expressed by formula XVII or XIX are stable against heatand ultraviolet irradiation, and thus they do not cause deteriorationunder ordinary conditions even when filled in liquid crystal panels.Compounds having a conjugated diene chain at a molecular terminal andexpressed by formula XXI, XXII, XXIII, or XXIV have a large ratio ofelastic constants, and are useful. Further, compounds containingfluorine atom and expressed by formula XVIII, XX, XXII, or XXIV have awide range of liquid crystal temperature and a low viscosity inparticular, and thus they are useful compounds.

On the other hand, when attention is paid to the number of ring in amolecule, compounds of the present invention can be developed intotwo-ring system compounds expressed by formula XXV, three-ring systemcompounds expressed by formula XXVI, or four-ring system compoundsexpressed by formula XXVII. Among these compounds of the presentinvention, so-called two-ring system compounds expressed by formula XXVare excellent materials because the range of liquid crystal can beadjusted around room temperature, and crystals are hardly precipitatedeven when they are used as component of liquid crystal compositions.Besides, since the two-ring system compounds have a low viscositycompared with the three-ring system compounds and four-ring systemcompounds, display of a high response speed can be obtained when thetwo-ring system compounds are filed in liquid crystal panels. So-calledthree-ring system compounds expressed by formula XXVI have a highclearing point, exhibit a good miscibility, and have a large ratio ofelastic constants which is necessary for obtaining a good steepness.Further, any of compounds having the four-ring system structure andexpressed by formula XXVII are important as component of liquid crystalcompositions since they have a very high clearing point and a largeratio of elastic constants, and exhibit a comparatively large opticalanisotropy. ##STR13##

Among combinations of ring structures possible with the two-ring systemcompounds expressed by formula XXV, specific combinations exhibitingpreferable properties are shown by formulas XXV-1 to XXV-4; amongcombinations of ring structures possible with the three-ring systemcompounds expressed by formula XXVI, specific combinations exhibitingpreferable properties are shown by formulas XXVI-1 to XXVI-12; and amongcombinations of ring structures possible with the four-ring systemcompounds expressed by formula XXVII, specific combinations exhibitingpreferable properties are shown by formulas XXVII-1 to XXVII-24.##STR14##

Among these, compounds expressed by any one of formulas XXV-1, XXVI-1,5, 6, 7, 8, 9, and 10, and XXVII-1, 5, 6, 7, 8, 9, 10, and 13 to 24, andhaving two or more cyclohexane rings in a molecule are useful since theyhave a wide temperature range of liquid crystal and a low viscosity. Anyof the compounds expressed by any one of formulas XXV-2, XXV-4, XXV-2,4, 6, 8, 9, 10, 11, and 12, and XXVII-2, 4, 6, 8, 9, 10, 11, 12, 14, 16,18, 20, 21, 22, 23, and 24, and having a hetero ring exhibit a largedielectric anisotropy, and thus, they are important as component ofliquid crystal compositions. Further, compounds expressed by any one offormulas XXV-3, XXVI-1, 2, 3, and 4, and XXVII-1, 2, 3, 4, 13, 14, 15,and 16 can be used for providing liquid crystal compositions satisfyingtheir purposes by properly selecting substituents on the phenyl ring. Inthis connection, preferable examples of phenyl group to which thesubstituent is introduced are shown in formulas i to xxvii. ##STR15##

Any of the compounds of the present invention having, at a terminal,phenyl ring shown by any one of formulas iv, v, vi, vii, viii, ix, x, orxi in which fluorine atom, chlorine atom, methyl or methoxy grouphydrogen atom of which is replaced by fluorine atom, or cyano group eachhaving a strong electron atractivity, is introduced at para-positionhave a large dielectric anisotropy, low viscosity, and wide liquidcrystal temperature range, and thus, they are important compounds forimparting dielectric property to liquid crystal compositions inparticular. Further, compounds of the present invention having phenylring which has the electron attractive substituent described above andone or two fluorine atoms thereon and expressed by any one of formulasxxii to xxvii have a larger dielectric anisotropy, and thus, they arematerials necessary for driving liquid crystal display devices at a lowvoltage. Compounds of the present invention having any one of phenylrings (i to iii) in which an alkyl group, an alkoxy group, or analkoxyalkyl group all of which are a weak electron-donating group do nothave a large dipole moment. These compounds are characterized by theirlow viscosity and good miscibility, and are useful in the aspect thatthey can be used for the purpose of controlling physical properties ofthe whole liquid crystal compositions to required values.

Next, among compounds of the present invention expressed by formula XXV,XXVI, or XXVII in which a bonding group or groups B¹, B¹ and B², or B¹,B², and B³ at internal positions are also included, specific examples ofcompounds which impart preferable properties are expressed by any one offormulas XXV-a to h, XXVI-a to p, and XXVII-a to s. ##STR16##

Among these specific compounds, compounds expressed by any one offormulas XXV-a, XXVI-a to h, XXVI-o and p, and XXVII-a to s have atleast one covalent bond as internal group, and exhibit a low viscosityand good miscibility. Compounds expressed by XXV-b, XXVI-b, and h to m,and XXVII-b, h, and n, and having ethylene chain or ethylene chain andother bond together as internal group exhibit a good liquidcrystallinity and low viscosity, and have a good miscibility. Compoundsexpressed by any one of formulas XXV-c and d, XXVI-c, j, and o, andXXVII-c, l, and o, and having oxymethylene chain or oxymethylene chainand other bond together as internal group exhibit a medium extent ofdielectric anisotropy and wide range of liquid crystal temperature, andare stable. Thus those compounds are useful. Compounds expressed by anyone of formulas XXV-e and f, XXVI-d, e, k, Q, and p, and XXVII-d, e, j,k, p, and q, and having an ester group such as oxycarbonyl orcarbonyloxy group, or the ester group and other group together asinternal group exhibit a large dielectric anisotropy and sufficientlywide range of liquid crystal temperEthenyland thus they are useful.Ethenylene derivatives expressed by any one of formulas XXV-g, XXVI-fand m, and XXVII-f and Q have a particularly wide range of liquidcrystal temperature and low viscosity. Also, these compounds have suchan advantage that when they are used as a component of liquid crystalcompositions, the compositions hardly exhibit a smectic phase. Further,butenyl derivatives expressed by any one of formulas XXV-h, XXVI-g andn, and XXVII-g, m, and s exhibit a good miscibility and low viscosity,and thus they are preferable compounds.

Method of preparation

Compounds of the present invention expressed by general formula I can besynthesized, for instance, by the method described below.

Compounds expressed by general formula I wherein R² represents a groupexpressed by formula II and X represents hydrogen atom:

The compounds can be obtained in a good yield by reacting a reactionagent prepared from diethylcyanomethyl phosphonate and a base with analdehyde derivative expressed by formula XXVIII ##STR17## wherein R¹,A¹, B¹, A², n1, B², A³, n2, B³, and n3 have the same meaning as definedabove, in a non-protic polar solvent under a low temperature condition.While the product in this reaction is sometimes obtained as a mixture oftwo isomers, that is, E-isomer and Z-isomer, derived from the portion ofdouble bond, only E-isomer having better properties as liquid crystalmaterial can be isolated by a purification and separation procedure suchas recrystallization and distillation, if necessary.

The compounds can also be obtained by the following method:

Halogenized vinyl derivative expressed by formula XXIX ##STR18## whereinR¹, A¹, B¹, A², n1, B², A³, n2, B³, and n3 have the same meaning asdefined above, and Y represents iodine or bromine atom,

is reacted with a metal cyanide in a non-protic polar solvent. In thiscase, copper cyanide and sodium cyanide can be mentioned as the metalcyanide. Further, this reaction can preferably be carried out underreflux conditions of the solvent to be used. As preferable solvent,acetone, dioxane, dimethylformamide, N-methylpyrrolidone, pyridine, andtetrahydrofuran can be mentioned.

Compounds expressed by general formula I wherein R² represent a groupexpressed by formula III and X represents hydrogen atom:

The compounds can be obtained in a good yield by reacting an α-βunsaturated aldehyde expressed by formula XXX ##STR19## wherein R¹, A¹,B¹, A², n1, B², A³, n2, B³, and n3 indicate the same meaning as definedabove,

in a non-protic polar solvent under a low temperature with a reagentprepared from diethylcyano-methyl phosphonate and a base. Since thisreaction proceeds retaining the steric conformation of reactants, theα-β unsaturated aldehyde which is a starting material must be a mixtureof steric isomers, or E-isomer. While the product of this reaction issometimes a mixture of two isomers, that is, E-isomer and Z-isomer,derived from the portion of double bond, only E-isomer having propertiesas better liquid crystal material can be isolated by a purification andseparation procedure such as recrystallization and distillation, ifnecessary.

Compounds expressed by general formula I wherein R² represents a groupexpressed by formula II, and X represents fluorine atom:

Dihalide expressed by formula XXXI ##STR20## wherein R¹, A¹, B¹, A², n1,B², A³, n2, B³, and n3 have the same meaning as defined above, and Yrepresents iodine or bromine atom,

is converted into a cyanide in a non-protic solvent such asN-methylpyrrolidone by using a metal cyanide. Since this reactionproceeds while retaining the steric conformation of reactants, thedihalide which is a starting material must be a mixture of isomers orE-isomer only. As the metal cyanide used in the cyanization reaction,copper cyanide and sodium cyanide are preferable. Also, this reaction ispreferably carried out under reflux conditions of the solvent to be usedin particular.

Compounds expressed by general formula I wherein R² represents a groupexpressed by formula III, and X represents fluorine atom:

Dihalide expressed by formula XXXII ##STR21## wherein R¹, A¹, B¹, A²,n1, B², A³, n2, B³, and n3 have the same meaning as defined above, and Yrepresents iodine or bromine atom,

is converted into a cyanide in a non-protic solvent such asN-methylpyrrolidone by using a metal cyanide. Since this reactionproceeds retaining the steric conformation of reactants, the dihalidewhich is a starting material must be a mixture containing an EE-isomeror EE-isomer only. As the metal cyanide used in the cyanizationreaction, copper cyanide and sodium cyanide are preferable. Also, thisreaction is preferably carried out under reflux conditions of thesolvent to be used in the aspect that the yield is good.

Among the starting materials used in each of the reactions describedabove, compounds expressed by formula XXVIII can be produced byoxidizing a corresponding alcohol derivative by using, for example, anoxidizing agent such as PCC, or produced through such a synthesis routas described in Laid-open Japanese Patent Publication No. Hei 01-175,947or WO 93/07,234. Halogenized vinyl derivatives expressed by formula XXIXcan be produced by a method described in WO 93/07,234.

α-β unsaturated aldehydes expressed by formula XXX can be synthesizedby, when n3 is 0, reacting a ketone derivative expressed by formulaXXXIII ##STR22## wherein R¹, A¹, B¹, A², n1, B², A³, n2, B³, and n3 havethe same meaning as defined above,

on the other hand, when n3 is 1, by reacting an aldehyde derivativeexpressed by formula XXXIV ##STR23## wherein R¹, A¹, B¹, A², n1, B², A³,n2, B³, and n3 have the same meaning as defined above

with a Wittig's reagent prepared from 1,3-dioxane-2-ylethyltriphenylphosphonium bromide and a base to once convert the ketone derivative oraldehyde derivative into compounds expressed by formula XXXV or XXXVI##STR24## wherein R¹, A¹, B¹, A², n1, B², A³, n2, B³, and n3 have thesame meaning as defined above,

and then treating with an acid.

Further, the dihalides expressed by formula XXXI are obtained bytreating an aldehyde derivative expressed by formula XXIII in a suitablesolvent such as ethylene glycol dimethyl ether with a reaction agentprepared from tribromofluoromethane and triphenylphosphine. Products inthis case usually become a mixture of E-isomer and Z-isomer derived fromthe steric conformation of olefin. While the products can be used asthey are for a succeeding reaction, they can be used for a succeedingreaction after isolation of only Z-isomer by carrying out a purificationprocedure such as a column chromatography, if necessary.

Finally, the dihalides expressed by formula XXXII can be obtained bytreating an α-β unsaturated aldehyde expressed by formula XXX in asuitable solvent such as ethylene glycol dimethyl ether with a reactionagent prepared from tribromofluoromethane and triphenyl phosphine.Products in this case usually become a mixture of E-isomer and Z-isomerderived from the steric conformation of olefin. While the products canbe used as they are for a succeeding reaction, they can be used for asucceeding reaction after separation of only Z-isomer by carrying out apurification procedure such as chromatography, if necessary.

Any of the liquid crystalline compounds of the present inventionobtained by such methods have a high clearing point and large ratio ofelastic constants (k₃₃ /k₁₁), and are remarkably excellent as componentof nematic liquid crystal compositions including for TFT mode,particularly as component of liquid crystal compositions for STN displaymode.

While the liquid crystal compositions provided by the present inventionmay be comprised only of a first component comprising at least oneliquid crystalline compound expressed by general formula I, thecompositions in which at least one compound (hereinafter referred to asa second A component) selected from the group consisting of thecompounds expressed by any one of the general formulas IV, V, and VIdescribed above and/or at least one compound (hereinafter referred to assecond B component) selected from the group consisting of the compoundsexpressed by any one of the general formulas VII, VIII, IX, X, and XIdescribed above is added in addition to the first component arepreferable. Further, known compounds may be mixed as a third componentfor the purposes of adjusting threshold voltage, temperature range ofliquid crystal, optical anisotropy (Δn), dielectric anisotropy(Δ.di-elect cons.), and viscosity.

Among the second A component, as preferable examples expressed bygeneral formula IV, the compounds expressed by any one of formulas IV-1to IV-12 can be mentioned, and as preferable compounds expressed bygeneral formula V, compounds of formulas V-1 to V-18, and as preferablecompounds expressed by general formula VI, compounds of formulas VI-1 toVI-18 can be mentioned, respectively. ##STR25## wherein R³ represents analkyl group.

Compounds expressed by any one of general formulas IV to VI have apositive dielectric anisotropy, and are remarkably excellent in heatstability and chemical stability, and thus, they are useful compoundswhen liquid crystal compositions for TFT (AM-LCD) of which a highreliability such as an especially high voltage holding ratio or a highspecific resistance required are produced.

While the compounds can be used in any range of amount based on thetotal weight of liquid crystal composition when liquid crystalcompositions for TFT are produced, the amount to be used is preferably10 to 97% by weight, and more preferably 40 to 95% by weight.

Among the second B component described above, as preferable examples ofthe compounds expressed by general formula VII, VIII, or IX, compoundsexpressed by any one of formulas VII-1 to VII-20, VIII-1 to VIII-3, andIX-1 to IX-11 can be mentioned, respectively. ##STR26## wherein R⁴, R⁵,and R⁶ represent an alkyl group or alkenyl group, and R' represents analkylene.

Compounds expressed by these general formulas VII to IX have a largepositive dielectric anisotropy, and are used as component of liquidcrystal compositions for the purpose of particularly reducing thresholdvoltage. Also, the compounds are used for the purpose of adjustingviscosity and optical anisotropy (Δn), and widening the range of nematictemperature such as raising clearing point, as well as for the purposeof improving steepness.

Further, among the second B component, as preferable examples ofcompounds expressed by general formula X or XI, compounds expressed byany one of formulas X-1 to X-15, and XI-1 to XI-13 can be mentioned,respectively. ##STR27## wherein R⁷, R⁸, R⁹, and R¹⁰ represent an alkylgroup.

Compounds expressed by general formula X or XI have a negative or smallpositive dielectric anisotropy. Among them, the compounds expressed bygeneral formula X are used for the purposes of mainly reducing theviscosity of the compositions and adjusting Δn. Compounds expressed bygeneral formula XI are used for the purpose of enhancing the range ofnematic temperature such as raising the clearing point of compositionsand/or the purpose of adjusting Δn. Accordingly, the compounds expressedby any one of general formulas VII to XI are useful when liquid crystalcompositions particularly for STN display mode or TN display mode areproduced.

While the compounds can be used in any range of amount depending ontheir purposes when liquid crystal compositions for TN display mode orSTN display mode are produced, the amount to be used is preferably 10 to97% by weight and preferably 40 to 95% by weight.

As described above, while the liquid crystal compositions for TFT may becomposed of the first component and the second A component, thecompositions may partially comprise the second B component. While theliquid crystal compositions for STN and TN may be composed of the firstcomponent and the second B component, the compositions may partiallycomprise the second component A.

Further, these liquid crystal compositions may further be added with thethird component described above, and the compounds expressed by any oneof formulas XII-1 to XII-35 can be mentioned as preferable examples.##STR28##

Liquid crystal compositions provided by the present invention preferablycontain at least one liquid crystalline compound expressed by generalformula I in the range of 0.1 to 99% by weight to develop excellentproperties.

Liquid crystal compositions of the present invention can be furtheroptimized by adding a suitable additive depending on intended uses. Assuch additive, for example, some compounds are described as chiraladditive in the literature. Such additive is added to cause the helicalstructure of liquid crystal and adjusting necessary twist angle, and toprevent reverse twisting. Liquid crystal compositions of the presentinvention optimized by such method can be produced by methods which areconventional by themselves, for instance, by a method in which severalliquid crystalline compounds to be contained in the liquid crystalcomposition are dissolved with each other at a temperature higher thanroom temperature. The composition thus produced is filled in a liquidcrystal cell to obtain a liquid crystal display device having a widerange of driving temperature and a high response speed.

Examples of the liquid crystal compositions comprising the compounds ofthe present invention are shown below, in which the number of compoundis the same as that shown in Examples described below.

Further, the compounds are designated according to the definition shownin Table 1 below, and specifically, left side terminal groups areindicated by n-, nO-, nOm-, V-, Vn-, nVm-, nVmVk-, or C- (wherein n, m,and k are an integer of 1 or greater), bonding groups are indicated by2, 4, E, T, V, CP20, or OCP2, ring structures are indicated by B, B(F),B(F,F), H, Py, D, or Ch, and right side terminal groups are indicated by-F, -CL, -C, -CF3, -OCF3, -OCF2H, -n, -On, -EMe, -nV, -mVn, -mVn, -VFF,-V2F, -nVC, -VVC, or -VCF (wherein n and m are an integer of 1 orgreater), respectively.

                  TABLE 1                                                         ______________________________________                                                               Symbol                                                 ______________________________________                                        Left side                                                                       terminal group                                                                C.sub.n H.sub.2n+1 -- n--                                                     C.sub.n H.sub.2n+1 O-- nO--                                                   C.sub.n H.sub.2n+1 OC.sub.m H.sub.2m -- nOm--                                 CH.sub.2 ═CH-- V--                                                        CH.sub.2 ═CHC.sub.n H.sub.2n -- Vn--                                      C.sub.n H.sub.2n+1 CH═CHC.sub.m H.sub.2m -- nVm--                         C.sub.n H.sub.2n+1 CH═CHC.sub.m H.sub.2m CH═CHC.sub.k H.sub.2k                               -- nVmVk--                                             NC-- C--                                                                      Bonding group                                                                 --C.sub.2 H.sub.4 -- 2                                                        --C.sub.4 H.sub.8 -- 4                                                        --COO-- E                                                                     --C.tbd.C-- T                                                                 --CH═CH-- V                                                               --CF.sub.2 O-- CF2O                                                           --OCF.sub.2 -- OCF2                                                           Ring structure                                                                 -                                                                                                   1  B R29##                                              -                                                                                                   2  B(F) ##                                              -                                                                                                   3  B(F,F)                                               -                                                                                                   4  H R32##                                              -                                                                                                   5  Py 33##                                              -                                                                                                   6  D R34##                                              -                                                                                                   7  Ch 35##                                              - Right side                                                                 terminal group                                                                --F --F                                                                       --Cl --CL                                                                     --CN --C                                                                      --CF.sub.3 --CF3                                                              --OCF.sub.3 --OCF3                                                            --OCF.sub.2 H --OCF2H                                                         --C.sub.n H.sub.2n+1 --n                                                      --OC.sub.n H.sub.2n+1 --On                                                    --COOCH.sub.3 --EMe                                                           --C.sub.n H.sub.2n CH═CH.sub.2 --nV                                       --C.sub.m H.sub.2m CH═CHC.sub.n H.sub.2n+1 --mVn                          --CH═CF.sub.2 --VFF                                                       --CH═CHC.sub.2 H.sub.4 --F --V2F                                          --C.sub.n H.sub.2n CH═CH--CN --nVC                                        --CH═CH--CN --VC                                                          --CH═CHCH═CH--CN --VVC                                                --CH═CF--CN --VCF                                                       ______________________________________                                    

Percent (%) showing the content of each compound in the CompositionExamples below means % by weight.

    ______________________________________                                        Composition Example 1                                                           2-HH--VC (No. 1) 4%                                                           3-HH--VC (No. 2) 3%                                                           4-HH--VC (No. 3) 3%                                                           5-HH--VC (No. 4) 3%                                                           7-HB(F)--F  4%                                                                5-H2B(F)--F  4%                                                               2-HHB(F)--F  12%                                                              3-HHB(F)--F  12%                                                              5-HHB(F)--F  12%                                                              2-H2HB(F)--F  4%                                                              3-H2HB(F)--F  2%                                                              5-H2HB(F)--F  4%                                                              2-HBB(F)--F  4%                                                               3-HBB(F)--F  4%                                                               5-HBB(F)--F  8%                                                               2-HBB--F  3%                                                                  3-HBB--F  3%                                                                  5-HBB--F  2%                                                                  3-HHB--F  4%                                                                  3-HHB-1  5%                                                                   Composition Example 2                                                         2-HH--VVC (No. 201) 4%                                                        3-HH--VVC (No. 202) 4%                                                        5-HH--VVC (No. 204) 5%                                                        3-HB--CL  4%                                                                  5-HB--CL  4%                                                                  7-HB--CL  4%                                                                  2-HHB--CL  6%                                                                 3-HHB--CL  6%                                                                 5-HHB--CL  6%                                                                 2-HBB(F)--F  6%                                                               3-HBB(F)--F  6%                                                               5-HBB(F)--F  12%                                                              3-HBB(F,F)--F  12%                                                            5-HBB(F,F)--F  12%                                                            3-H-2-HB(F)--CL  3%                                                           3-HB(F)TB-2  3%                                                               3-HB(F)VB-2  3%                                                               Composition Example 3                                                         3-H2H--VC (No. 7) 7%                                                          3-HH-2VC (No. 102) 7%                                                         7-HB(F,F)--F  7%                                                              3-HHB(F,F)--F  7%                                                             4-HHB(F,F)--F  5%                                                             3-H2HB(F,F)--F  10%                                                           4-H2HB(F,F)--F  8%                                                            5-H2HB(F,F)--F  8%                                                            3-HH2B(F,F)--F  12%                                                           5-HH2B(F,F)--F  7%                                                            3-HBB(F,F)--F  8%                                                             5-HBB(F,F)--F  8%                                                             3-HHBB(F,F)--F  3%                                                            3-HH2BB(F,F)--F  3%                                                           Composition Example 4                                                         5-BH--VC (No. 13) 7%                                                          F--BH--VC (No. 802) 7%                                                        7-HB(F)--F  7%                                                                2-HHB(F)--F  8%                                                               3-HHB(F)--F  8%                                                               5-HHB(F)--F  8%                                                               2-H2HB(F)--F  6%                                                              3-H2HB(F)--F  3%                                                              5-H2HB(F)--F  6%                                                              2-HHB(F,F)--F  5%                                                             3-HHB(F,F)--F  5%                                                             3-HHEB(F,F)--F  5%                                                            3-HBEB(F,F)--F  3%                                                            3-HHB--CL  5%                                                                 3-HHEB--F  3%                                                                 5-HHEB--F  3%                                                                 3-HBEB--F  3%                                                                 3-HHB-1  4%                                                                   3-HHB-01  4%                                                                  Composition Example 5                                                         C--BH--VC (No. 801) 5%                                                        5-BH--VC (No. 13) 5%                                                          4-HH--VC (No. 3) 6%                                                           3-HH--VVC (No. 202) 6%                                                        7-HB(F)--F  10%                                                               2-HHB(F)--F  12%                                                              3-HHB(F)--F  12%                                                              5-HHB(F)--F  12%                                                              2-HBB(F)--F  3%                                                               3-HBB(F)--F  3%                                                               5-HBB(F)--F  6%                                                               3-HHB--F  5%                                                                  3-HHEBB--F  3%                                                                5-HHEBB--F  3%                                                                3-HB--O2  3%                                                                  3-HHB-1  3%                                                                   3-HHB-3  3%                                                                   Composition Example 6                                                         3-HH--VCF (No. 402) 6%                                                        4-HH--VCF (No. 403) 6%                                                        5-HH--VCF (No. 404) 6%                                                        3O1-BEB(F)--CN  5%                                                            2-HB--CN  5%                                                                  3-HB--CN  15%                                                                 2-HHB--CN  5%                                                                 3-HHB--CN  5%                                                                 4-HHB--CN  5%                                                                 3-PyBB--F  10%                                                                3-HH-4  7%                                                                    3-HH-5  2%                                                                    2-BTB--O1  3%                                                                 3-BTB--O1  3%                                                                 4-BTB--O1  3%                                                                 4-BTB--O2  3%                                                                 5-BTB--O1  3%                                                                 3-HHB-1  5%                                                                   3-HHB--O1  3%                                                                 Composition Example 7                                                         3-BHH--VC (No. 21) 10%                                                        3-HH--VC (No. 2) 10%                                                          V2-HB--C  10%                                                                 1V2-HB--CN  10%                                                               3-HB--CN  5%                                                                  3-HHB--CN  5%                                                                 3-PyBB--F  7%                                                                 2-PyBH-3  4%                                                                  3-PyBH-3  4%                                                                  4-PyBH-3  4%                                                                  3-HH-4  8%                                                                    1O1-HH-3  4%                                                                  2-BTB-1  4%                                                                   1-BTB-6  8%                                                                   4-BTB-4  4%                                                                   3-HHB-1  3%                                                                   Composition Example 8                                                         4-HH--VC (No. 3) 6%                                                           4-HH--VVC (No. 203) 6%                                                        4-HH--VCF (No. 403) 7%                                                        2-BB--C  7%                                                                   1O1-HB--C  8%                                                                 2O1-HB--C  8%                                                                 2-BEB--C  3%                                                                  3-DB--C  3%                                                                   5-PyB--F  6%                                                                  3-PyBB--F  6%                                                                 2-PyB-2  3%                                                                   3-PyB-2  3%                                                                   4-PyB-2  3%                                                                   2-PyBH-3  4%                                                                  3-PyBH-3  4%                                                                  4-PyBH-3  4%                                                                  3-PyB--O2  3%                                                                 2-HHB-1  4%                                                                   3-HHB-1  5%                                                                   3-HHB-3  7%                                                                   Composition Example 9                                                         3-H2H--VC (No. 7) 8%                                                          5-BH--VC (No. 13) 8%                                                          5-HH--VCF (No. 404) 8%                                                        3-PyB(F)--F  7%                                                               3-PyBB--F  4%                                                                 4-PyBB--F  4%                                                                 5-PyBB--F  4%                                                                 2-PyB-2  5%                                                                   3-PyB-2  5%                                                                   4-PyB-2  5%                                                                   3-HEB--O4  5%                                                                 4-HEB--O2  5%                                                                 5-HEB--O2  5%                                                                 2-H2BTB-4  4%                                                                 3-H2BTB-4  4%                                                                 3-HHB-1  5%                                                                   3-HHB-3  5%                                                                   3-HHEBB--C  3%                                                                5-HHEBB--C  3%                                                                3-HBEBB--C  3%                                                                Composition Example 10                                                        2-HH--VVC (No. 201) 7%                                                        C--BH--VC (No. 801) 7%                                                        3-HH-2VC (No. 102) 7%                                                         2O1-BEB(F)--C  3%                                                             3O1-BEB(F)--C  10%                                                            2-HB(F)--C  8%                                                                3-HB(F)--C  9%                                                                3-HHB(F)--C  3%                                                               2-HHB(F)--F  5%                                                               3-HHB(F)--F  5%                                                               5-HHB(F)--F  5%                                                               3-HHB-1  5%                                                                   3-HHB-3  4%                                                                   3-HHB--O1  4%                                                                 3-H2BTB-2  3%                                                                 3-H2BTB-3  3%                                                                 3-H2BTB-4  3%                                                                 3-HB(F)TB-2  3%                                                               3-HB(F)TB-3  3%                                                               3-HB(F)TB-4  3%                                                               Composition Example 11                                                        3-HH--VVC (No. 202) 5%                                                        3-BHH--VC (No. 21) 9%                                                         F--BH--VC (No. 802) 5%                                                        2V--HB--C  9%                                                                 1V2-HB--C  9%                                                                 3-HB--C  13%                                                                  5-HB--C  7%                                                                   1O1-HB--C  5%                                                                 2O1-HB--C  5%                                                                 3-HHB--F  4%                                                                  3-HH-4  4%                                                                    2-BTB--O1  6%                                                                 3-HHB--O1  4%                                                                 3-HHB-1  4%                                                                   3-HHB-3  7%                                                                   3-HB(F)TB-2  4%                                                               Composition Example 12                                                        5-HH--VC (No. 4) 5%                                                           3-H2H--VC (No. 7) 6%                                                          C--BH--VC (No. 801) 5%                                                        3-BHH--VC (No. 21) 6%                                                         1V2-BEB(F,F)--C  15%                                                          3O1-BEB(F)--C  15%                                                            3-HB--C  12%                                                                  3-HB(F)--C  10%                                                               3-HHB(F)--C  8%                                                               3-PyBB--F  6%                                                                 4-PyBB--F  6%                                                                 5-PyBB--F  6%                                                                 Composition Example 13                                                        4-HH--VVC (No. 203) 5%                                                        5-BH--VC (No. 13) 5%                                                          5-HH--VCF (No. 404) 5%                                                        F--BH--VC (No. 802) 5%                                                        3O1-BEB(F)--C  8%                                                             4O1-BEB(F)--C  5%                                                             2-HHB(F)--F  4%                                                               3-HHB(F)--F  4%                                                               5-HHB(F)--F  4%                                                               3-HHEB--F  3%                                                                 5-HHEB--F  3%                                                                 3-HEB--F  3%                                                                  3-HH-EMe  8%                                                                  3-HEB--O4  4%                                                                 3-HEB-3  4%                                                                   3-HEB-4  4%                                                                   2-PyBH-3  4%                                                                  3-PyBH-3  4%                                                                  4-PyBH-3  4%                                                                  3-HB--O2  10%                                                                 3-HHB-1  4%                                                                   Composition Example 14                                                        3-HH--VC (No. 2) 7%                                                           3-H2H--VC (No. 7) 7%                                                          3-HH-2VC (No. 102) 7%                                                         5-HB--F  8%                                                                   7-HB--F  8%                                                                   2-HHB--OCF3  5%                                                               3-HHB--OCF3  5%                                                               5-HHB--OCF3  5%                                                               3-HHB(F,F)--OCF2H  15%                                                        5-HHB(F,F)--OCF2H  15%                                                        3-HB(F,F)B(F)--F  6%                                                          5-HB(F,F)B(F)--F  6%                                                          3-HHEB--OCF3  3%                                                              5-HHEB--OCF3  3%                                                              Composition Example 15                                                        C--BH--VC (No. 801) 5%                                                        3-HH--VCF (No. 402) 5%                                                        5-HH--VCF (No. 404) 5%                                                        3-BHH--VC (No. 21) 5%                                                         5-HB--F  8%                                                                   6-HB--F  8%                                                                   7-HB--F  8%                                                                   2-HHB--OCF3  6%                                                               3-HHB--OCF3  6%                                                               4-HHB--OCF3  6%                                                               5-HHB--OCF3  6%                                                               3-HH2B--OCF3  5%                                                              5-HH2B--OCF3  5%                                                              3-HBB(F)--F  8%                                                               5-HBB(F)--F  8%                                                               3-HB(F)BH-3  3%                                                               5-HB(F)BH-3  3%                                                               Composition Example 16                                                        2-HH--VC (No. 1) 9%                                                           3-BHH--VC (No. 21) 8%                                                         4-HH--VCF (No. 403) 8%                                                        V1-HB--C  3%                                                                  4-BB-2  3%                                                                    3-BB--C  5%                                                                   5-BB--C  5%                                                                   2-HB(F)--C  5%                                                                3-H2B--O2  4%                                                                 5-H2B--O3  8%                                                                 3-BEB--C  5%                                                                  5-HEB--O1  6%                                                                 5-HEB--O3  6%                                                                 5-BBB--C  3%                                                                  4-BPyB--C  3%                                                                 4-BPyB-5  3%                                                                  5-HB2B-4  3%                                                                  5-HBB2B-3  3%                                                                 1V-HH-1O1  5%                                                                 1V2-HBB-3  5%                                                                 Composition Example 17                                                        5-BH--VC (No. 13) 10%                                                         F--BH--VC (No. 802) 10%                                                       4-HEB(F)--F  5%                                                               5-HEB(F)--F  5%                                                               2-BEB(F)--C  4%                                                               3-BEB(F)--C  4%                                                               4-BFB(F)--C  6%                                                               5-BEB(F)--C  6%                                                               1O3-HB(F)--C  6%                                                              3-HHEB(F)--F  4%                                                              5-HHEB(F)--F  4%                                                              2-HBEB(F)--F  5%                                                              3-HBEB(F)--F  5%                                                              4-HBEB(F)--F  5%                                                              5-HBEB(F)--F  5%                                                              3-HBTB-2  10%                                                                 V2-HH-3  3%                                                                   V2-HHB-1  3%                                                                ______________________________________                                    

Now, the present invention will be described in more detail withreference to Examples. However, it should be understood that the presentinvention is by no means restricted by such specific Examples. In theExamples, symbols C, N, S_(A), S_(B), S_(E), and I indicate crystalphase, nematic phase, Smectic A phase, Smectic B phase, Smectic E phase,and isotropic liquid phase, respectively, and combined symbols means thephase transition temperature between the combined phases. In thisconnection, CC' show a transition temperature of crystal-crystal.

EXAMPLE 1

Preparation of1-cyano-2-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)ethene [Compoundexpressed by general formula I wherein R¹ represents ethyl group, A¹represents 1,4-cyclohexylene, B¹ represents a covalent bond, n1 is 0, n2is 0, n3 is 0, R² represents a group expressed by formula II, and Xrepresents hydrogen atom (Compound No. 1)]

To a solution prepared by dissolving 17.5 g of diethyl cyanomethylphosphonate in 200 ml of tetrahydrofuran, was added 4.0 g of an oildispersion of sodium hydride (60%) at -50° C., and then the solution wasstirred for 30 min. To this solution was added a tetrahydrofuransolution containing 12 g of trans-4-(trans-4-ethylcyclohexyl)cyclohexanecarboaldehyde. Reaction solution was stirred at -50° C. for 15 min, itstemperature was gradually raised up to room temperature, a dilutehydrochloric acid was added to the solution, and the solution wasextracted with toluene. After the organic layer was washed with water,it was dried by using anhydrous magnesium sulfate, and concentratedunder a reduced pressure to obtain a brown oily product. The product waspurified by using a silica gel column chromatography, and thenrecrystallized from heptane to obtain 5.1 g of the subject compound.

NI 132.0° C.

S_(B) N 75.0 to 76.1° C.

CS_(B) 46.5° C.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 2 to 9) are synthesized.

Compound No.

2 1-cyano-2-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)ethene

NI 161.3 to 162.2° C.

S_(A) N 65.1 to 65.5° C.

S_(B) S_(A) 58.2 to 59.3° C.

S_(E) S_(B) 56.7 to 57.4° C.

CS_(E) 38.9 to 39.3° C.

3 1-cyano-2-(trans-4-(trans-4-butylcyclohexyl)cyclohexyl)ethene

NI 174.4 to 175.3° C.

S_(A) N 84.9 to 85.8° C.

S_(B) S_(A) 83.9 to 84.5° C.

CS_(B) Lower than 15° C.

4 1-cyano-2-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)ethene

NI 154.4° C.

S_(B) N 83.4 to 84.4° C.

CS_(B) Lower than 15° C.

5 1-cyano-2-(trans-4-(trans-4-heptylcyclohexyl)cyclohexyl)ethene

6 1-cyano-2-(trans-4-(2-(trans-4-ethylcyclohexyl)ethyl)cyclohexyl)ethene

71-cyano-2-(trans-4-(2-(trans-4-propylcyclohexyl)ethyl)cyclohexyl)ethene

NI 131.6° C.

(S_(A) N 50.6° C. S_(B) S_(A) 44.1° C.)

CN 50.7° C.

81-cyano-2-(trans-4-(2-(trans-4-pentylcyclohexyl)ethyl)cyclohexyl)ethene

91-cyano-2-(trans-4-(2-(trans-4-heptylcyclohexyl)ethyl)cyclohexyl)ethene

EXAMPLE 2

Preparation of 1-cyano-2-(trans-4-(4-ethylphenyl)cyclohexyl)ethene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, n1 is0, n2 is 0, n3 is 0, R² represents a group expressed by formula II, andX represents hydrogen atom (Compound No. 10)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(4-ethylphenyl)cyclohexane carboaldehydewas used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 11 to 29) are synthesized.

11 1-cyano-2-(trans-4-(4-propylphenyl)cyclohexyl)ethene

12 1-cyano-2-(trans-4-(4-butylphenyl)cyclohexyl)ethene

13 1-cyano-2-(trans-4-(4-pentylphenyl)cyclohexyl)ethene

(NI 60.2 to 60.6° C.)

CI 67.3 to 67.8° C.

14 1-cyano-2-(trans-4-(4-heptylphenyl)cyclohexyl)ethene

15 1-cyano-2-(trans-4-(2-(4-ethylphenyl)ethyl)cyclohexyl)ethene

16 1-cyano-2-(trans-4-(2-(4-propylphenyl)ethyl)cyclohexyl)ethene

17 1-cyano-2-(trans-4-(2-(4-butylphenyl)ethyl)cyclohexyl)ethene

18 1-cyano-2-(trans-4-(2-(4-pentylphenyl)ethyl)cyclohexyl)ethene

19 1-cyano-2-(trans-4-(2-(4-heptylphenyl)ethyl)cyclohexyl)ethene

201-cyano-2-(trans-4-(trans-4-(4-methylphenyl)cyclohexyl)cyclohexyl)ethene

NI 297° C.

CN 97.3 to 98.4° C.

211-cyano-2-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)cyclohexyl)ethene

221-cyano-2-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)cyclohexyl)ethene

231-cyano-2-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)cyclohexyl)ethene

241-cyano-2-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)cyclohexyl)ethene

251-cyano-2-(trans-4-(2-(trans-4-(4-ethylphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

261-cyano-2-(trans-4-(2-(trans-4-(4-propylphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

271-cyano-2-(trans-4-(2-(trans-4-(4-butylphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

281-cyano-2-(trans-4-(2-(trans-4-(4-pentylphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

291-cyano-2-(trans-4-(2-(trans-4-(4-heptylphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

EXAMPLE 3

Preparation of1-cyano-2-(trans-4-(2-(trans-4-ethylcyclohexyl)ethenyl)cyclohexyl)ethene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-cyclohexylene, B¹ represents 1,2-ethenylene, n1is 0, n2 is 0, n3 is 0, R² represents a group expressed by formula II,and X represents hydrogen atom (Compound No. 30)]

Subject compound was synthesized by the same procedures as in Example 1with the exception thattrans-4-(2E-(trans-4-ethylcyclohexyl)ethenyl)cyclohexane carboaldehydewas used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 31 to 39) are synthesized.

311-cyano-2-(trans-4-(2E-(trans-4-propylcyclohexyl)ethenyl)cyclohexyl)ethene

321-cyano-2-(trans-4-(2E-(trans-4-butylcyclohexyl)ethenyl)cyclohexyl)ethene

331-cyano-2-(trans-4-(2E-(trans-4-pentylcyclohexyl)ethenyl)cyclohexyl)ethene

341-cyano-2-(trans-4-(2E-(trans-4-heptylcyclohexyl)ethenyl)cyclohexyl)ethene

351-cyano-2-(trans-4-(2E-(trans-4-(4-ethylphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

361-cyano-2-(trans-4-(2E-(trans-4-(4-propylphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

371-cyano-2-(trans-4-(2E-(trans-4-(4-butylphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

381-cyano-2-(trans-4-(2E-(trans-4-(4-pentylphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

391-cyano-2-(trans-4-(2E-(trans-4-(4-heptylphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

EXAMPLE 4

Preparation of trans-4-(2-cyanoethenyl)cyclohexyltrans-4-propylcyclohexane carboxylate [Compound expressed by generalformula I wherein R¹ represents propyl group, A¹ represents1,4-cyclohexylene, B¹ represents carbonyloxy, n1 is 0, n2 is 0, n3 is 0,R² represents a group expressed by formula II, and X represents hydrogenatom (Compound No. 40)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-formylcyclohexyltrans-4-propylcyclohexane carboxylate was used as starting materialinstead of trans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 41 to 70) are synthesized.

41 trans-4-(2-cyanoethenyl)cyclohexyl trans-4-ethylcyclohexanecarboxylate

42 trans-4-(2-cyanoethenyl)cyclohexyl trans-4-butylcyclohexanecarboxylate

43 trans-4-(2-cyanoethenyl)cyclohexyl trans-4-pentylcyclohexanecarboxylate

44 trans-4-(2-cyanoethenyl)cyclohexyl trans-4-hexylcyclohexanecarboxylate

45 trans-4-ethylcyclohexyl trans-4-(2-cyanoethenyl)cyclohexanecarboxylate

46 trans-4-propylcyclohexyl trans-4-(2-cyanoethenyl)cyclohexanecarboxylate

47 trans-4-butylcyclohexyl trans-4-(2-cyanoethenyl)cyclohexanecarboxylate

48 trans-4-pentylcyclohexyl trans-4-(2-cyanoethenyl)cyclohexanecarboxylate

49 trans-4-hexylcyclohexyl trans-4-(2-cyanoethenyl)cyclohexanecarboxylate

50 trans-4-(2-cyanoethenyl)cyclohexyl 4-ethylbenzoate

51 trans-4-(2-cyanoethenyl)cyclohexyl 4-propylbenzoate

52 trans-4-(2-cyanoethenyl)cyclohexyl 4-butylbenzoate

53 trans-4-(2-cyanoethenyl)cyclohexyl 4-pentylbenzoate

54 trans-4-(2-cyanoethenyl)cyclohexyl 4-hexylbenzoate

55 4-ethylphenyl trans-4-(2-cyanoethenyl)cyclohexane carboxylate

56 4-propylphenyl trans-4-(2-cyanoethenyl)cyclohexane carboxylate

57 4-butylphenyl trans-4-(2-cyanoethenyl)cyclohexane carboxylate

58 4-pentylphenyl trans-4-(2-cyanoethenyl)cyclohexane carboxylate

59 4-hexylphenyl trans-4-(2-cyanoethenyl)cyclohexane carboxylate

60 4-heptylphenyl trans-4-(2-cyanoethenyl)cyclohexane carboxylate

61 trans-4-(4-ethylphenyl)cyclohexyl trans-4-(2-cyanoethenyl)cyclohexanecarboxylate

62 trans-4-(4-propylphenyl)cyclohexyltrans-4-(2-cyanoethenyl)cyclohexane carboxylate

63 trans-4-(4-butylphenyl)cyclohexyl trans-4-(2-cyanoethenyl)cyclohexanecarboxylate

64 trans-4-(4-pentylphenyl)cyclohexyltrans-4-(2-cyanoethenyl)cyclohexane carboxylate

65 trans-4-(4-hexylphenyl)cyclohexyl trans-4-(2-cyanoethenyl)cyclohexanecarboxylate

66 trans-4-(2-cyanoethenyl)cyclohexyl trans-4-(4-ethylphenyl)cyclohexanecarboxylate

67 trans-4-(2-cyanoethenyl)cyclohexyltrans-4-(4-propylphenyl)cyclohexane carboxylate

68 trans-4-(2-cyanoethenyl)cyclohexyl trans-4-(4-butylphenyl)cyclohexanecarboxylate

69 trans-4-(2-cyanoethenyl)cyclohexyltrans-4-(4-pentylphenyl)cyclohexane carboxylate

70 trans-4-(2-cyanoethenyl)cyclohexyl trans-4-(4-hexylphenyl)cyclohexanecarboxylate

EXAMPLE 5

Preparation of1-cyano-2-(trans-4-(4-ethylphenyl)methoxycyclohexyl)ethene [Compoundexpressed by general formula I wherein R¹ represents ethyl group, A¹represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0, n2 is 0,n3 is 0, R² represents a group expressed by formula II, and X representshydrogen atom (Compound No. 71)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(4-ethylphenyl)methoxycyclohexanecarboaldehyde was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 72 to 87) are synthesized.

72 1-cyano-2-(trans-4-(4-propylphenyl)methoxycyclohexyl)ethene

73 1-cyano-2-(trans-4-(4-butylphenyl)methoxycyclohexyl)ethene

74 1-cyano-2-(trans-4-(4-pentylphenyl)methoxycyclohexyl)ethene

75 1-cyano-2-(trans-4-(4-heptylphenyl)methoxycyclohexyl)ethene

76 1-cyano-2-(trans-4-(trans-4-propylcyclohexyl)methoxycyclohexyl)ethene

77 1-cyano-2-(trans-4-(trans-4-pentylcyclohexyl)methoxycyclohexyl)ethene

78 1-cyano-2-(trans-4-(trans-4-heptylcyclohexyl)methoxycyclohexyl)ethene

791-cyano-2-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)methoxycyclohexyl)ethene

801-cyano-2-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)methoxycyclohexyl)ethene

811-cyano-2-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)methoxycyclohexyl)ethene

821-cyano-2-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)methoxycyclohexyl)ethene

831-cyano-2-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)methoxycyclohexyl)ethene

841-cyano-2-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)oxymethylcyclohexyl)ethene

851-cyano-2-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)oxymethylcyclohexyl)ethene

861-cyano-2-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)oxymethylcyclohexyl)ethene

871-cyano-2-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)oxymethylcyclohexyl)ethene

EXAMPLE 6

Preparation of1-cyano-2-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)ethene [Compoundexpressed by general formula I wherein R¹ represents propyl group, A¹represents 1,4-phenylene, B¹ represents 1,4-butylene, n1 is 0, n2 is 0,n3 is 0, R² represents a group expressed by formula II, and X representshydrogen atom (Compound No. 88)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(4-(4-propylphenyl)butyl)cyclohexanecarboaldehyde was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 89 to 100) are synthesized.

89 1-cyano-2-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)ethene

90 1-cyano-2-(trans-4-(4-(4-butylphenyl)butyl)cyclohexyl)ethene

91 1-cyano-2-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)ethene

92 1-cyano-2-(trans-4-(4-(4-heptylphenyl)butyl)cyclohexyl)ethene

931-cyano-2-(trans-4-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)cyclohexyl)ethene

941-cyano-2-(trans-4-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)cyclohexyl)ethene

951-cyano-2-(trans-4-(trans-4-(4-(4-butylphenyl)butyl)cyclohexyl)cyclohexyl)ethene

961-cyano-2-(trans-4-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)cyclohexyl)ethene

971-cyano-2-(trans-4-(4-(trans-4-(4-ethylphenyl)cyclohexyl)butyl)cyclohexyl)ethene

981-cyano-2-(trans-4-(4-(trans-4-(4-propylphenyl)cyclohexyl)butyl)cyclohexyl)ethene

991-cyano-2-(trans-4-(4-(trans-4-(4-butylphenyl)cyclohexyl)butyl)cyclohexyl)ethene

1001-cyano-2-(trans-4-(4-(trans-4-(4-pentylphenyl)cyclohexyl)butyl)cyclohexyl)ethene

EXAMPLE 7

Preparation of1-cyano-4-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents ethylgroup, ring A¹ represents 1,4-cyclohexylene, B¹ represents a covalentbond, n1 is 0, n2 is 0, n3 is 1, R² represents a group expressed byformula II, and X represents hydrogen atom (Compound No. 101)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)propanal was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 102 to 110) are synthesized.

102 1-cyano-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)-1-butene

NI 136.9° C.

S_(A) N 101.4° C.

S_(B) S_(A) 101.2° C.

CS_(B) 74.7° C.

103 1-cyano-4-(trans-4-(trans-4-butylcyclohexyl)cyclohexyl)-1-butene

104 1-cyano-4-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)-1-butene

105 1-cyano-4-(trans-4-(trans-4-heptylcyclohexyl)cyclohexyl)-1-butene

1061-cyano-4-(trans-4-(2-(trans-4-ethylcyclohexyl)ethyl)cyclohexyl)-1-butene

1071-cyano-4-(trans-4-(2-(trans-4-propylcyclohexyl)ethyl)cyclohexyl)-1-butene

1081-cyano-4-(trans-4-(2-(trans-4-butylcyclohexyl)ethyl)cyclohexyl)-1-butene

1091-cyano-4-(trans-4-(2-(trans-4-pentylcyclohexyl)ethyl)cyclohexyl)-1-butene

1101-cyano-4-(trans-4-(2-(trans-4-heptylcyclohexyl)ethyl)cyclohexyl)-1-butene

EXAMPLE 8

Preparation of 1-cyano-4-(trans-4-(4-propylphenyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents propylgroup, ring A¹ represents 1,4-phenylene, B¹ represents a covalent bond,n1 is 0, n2 is 0, n3 is 1, R² represents a group expressed by formulaII, and X represents hydrogen atom (Compound No. 111)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that 3-(trans-4-(4-propylphenyl)cyclohexyl)propanalwas used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 112 to 130) are synthesized.

112 1-cyano-4-(trans-4-(4-ethylphenyl)cyclohexyl)-1-butene

113 1-cyano-4-(trans-4-(4-butylphenyl)cyclohexyl)-1-butene

114 1-cyano-4-(trans-4-(4-pentylphenyl)cyclohexyl)-1-butene

115 1-cyano-4-(trans-4-(4-heptylphenyl)cyclohexyl)-1-butene

116 1-cyano-4-(trans-4-(2-(4-ethylphenyl)ethyl)cyclohexyl)-1-butene

117 1-cyano-4-(trans-4-(2-(4-propylphenyl)ethyl)cyclohexyl)-1-butene

118 1-cyano-4-(trans-4-(2-(4-butylphenyl)ethyl)cyclohexyl)-1-butene

119 1-cyano-4-(trans-4-(2-(4-pentylphenyl)ethyl)cyclohexyl)-1-butene

120 1-cyano-4-(trans-4-(2-(4-heptylphenyl)ethyl)cyclohexyl)-1-butene

1211-cyano-4-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)cyclohexyl)-1-butene

1221-cyano-4-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)cyclohexyl)-1-buten

1231-cyano-4-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)cyclohexyl)-1-butene

1241-cyano-4-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)cyclohexyl)-1-butene

1251-cyano-4-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)cyclohexyl)-1-butene

1261-cyano-4-(trans-4-(2-(trans-4-(4-ethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

1271-cyano-4-(trans-4-(2-(trans-4-(4-propylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

1281-cyano-4-(trans-4-(2-(trans-4-(4-butylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

1291-cyano-4-(trans-4-(2-(trans-4-(4-pentylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

1301-cyano-4-(trans-4-(2-(trans-4-(4-heptylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

EXAMPLE 9

Preparation of1-cyano-4-(trans-4-(2-(trans-4-ethylcyclohexyl)ethenyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents ethylgroup, ring A¹ represents 1,4-cyclohexylene, B¹ represents1,2-ethenylene, n1 is 0, n2 is 0, n3 is 1, R² represents a groupexpressed by formula II, and X represents hydrogen atom (Compound No.131)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that3-(trans-4-(2E-(trans-4-ethylcyclohexyl)ethenyl)cyclohexyl)propanal wasused as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 132 to 140) are synthesized.

1321-cyano-4-(trans-4-(2E-(trans-4-propylcyclohexyl)ethenyl)cyclohexyl)-1-butene

1331-cyano-4-(trans-4-(2E-(trans-4-butylcyclohexyl)ethenyl)cyclohexyl)-1-butene

1341-cyano-4-(trans-4-(2E-(trans-4-pentylcyclohexyl)ethenyl)cyclohexyl)-1-butene

1351-cyano-4-(trans-4-(2E-(trans-4-heptylcyclohexyl)ethenyl)cyclohexyl)-1-butene

1361-cyano-4-(trans-4-(2E-(trans-4-(4-ethylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

1371-cyano-4-(trans-4-(2E-(trans-4-(4-propylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

1381-cyano-4-(trans-4-(2E-(trans-4-(4-butylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

1391-cyano-4-(trans-4-(2E-(trans-4-(4-pentylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

1401-cyano-4-(trans-4-(2E-(trans-4-(4-heptylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

EXAMPLE 10

Preparation of trans-4-(4-cyano-3-butenyl)cyclohexyltrans-4-ethylcyclohexane carboxylate [Compound expressed by generalformula I wherein R¹ represents ethyl group, ring A¹ represents1,4-cyclohexylene, B¹ represents carbonyloxy, n1 is 0, n2 is 0, n3 is 1,R² represents a group expressed by formula II, and X represents hydrogenatom (Compound No. 141)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(2-formylethyl)cyclohexyltrans-4-ethylcyclohexane carboxylate was used as starting materialinstead of trans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 142 to 171) are synthesized.

142 trans-4-(4-cyano-3-butenyl)cyclohexyl trans-4-propylcyclohexanecarboxylate

143 trans-4-(4-cyano-3-butenyl)cyclohexyl trans-4-butylcyclohexanecarboxylate

144 trans-4-(4-cyano-3-butenyl)cyclohexyl trans-4-pentylcyclohexanecarboxylate

145 trans-4-(4-cyano-3-butenyl)cyclohexyl trans-4-hexylcyclohexanecarboxylate

146 trans-4-ethylcyclohexyl trans-4-(4-cyano-3-butenyl)cyclohexanecarboxylate

147 trans-4-propylcyclohexyl trans-4-(4-cyano-3-butenyl)cyclohexanecarboxylate

148 trans-4-butylcyclohexyl trans-4-(4-cyano-3-butenyl)cyclohexanecarboxylate

149 trans-4-pentylcyclohexyl trans-4-(4-cyano-3-butenyl)cyclohexanecarboxylate

150 trans-4-hexylcyclohexyl trans-4-(4-cyano-3-butenyl)cyclohexanecarboxylate

151 trans-4-(4-cyano-3-butenyl)cyclohexyl 4-ethyl benzoate

152 trans-4-(4-cyano-3-butenyl)cyclohexyl 4-propyl benzoate

153 trans-4-(4-cyano-3-butenyl)cyclohexyl 4-butyl benzoate

154 trans-4-(4-cyano-3-butenyl)cyclohexyl 4-pentyl benzoate

155 trans-4-(4-cyano-3-butenyl)cyclohexyl 4-hexyl benzoate

156 4-ethylphenyl trans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

157 4-propylphenyl trans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

158 4-butylphenyl trans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

159 4-pentylphenyl trans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

160 4-hexylphenyl trans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

161 4-heptylphenyl trans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

162 trans-4-(4-ethylphenyl)cyclohexyltrans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

163 trans-4-(4-propylphenyl)cyclohexyltrans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

164 trans-4-(4-butylphenyl)cyclohexyltrans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

165 trans-4-(4-pentylphenyl)cyclohexyltrans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

166 trans-4-(4-hexylphenyl)cyclohexyltrans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

167 trans-4-(4-cyano-3-butenyl)cyclohexyltrans-4-(4-ethylphenyl)cyclohexane carboxylate

168 trans-4-(4-cyano-3-butenyl)cyclohexyltrans-4-(4-propylphenyl)cyclohexane carboxylate

169 trans-4-(4-cyano-3-butenyl)cyclohexyltrans-4-(4-butylphenyl)cyclohexane carboxylate

170 trans-4-(4-cyano-3-butenyl)cyclohexyltrans-4-(4-pentylphenyl)cyclohexane carboxylate

171 trans-4-(4-cyano-3-butenyl)cyclohexyltrans-4-(4-hexylphenyl)cyclohexane carboxylate

EXAMPLE 11

Preparation of1-cyano-4-(trans-4-(4-ethylphenyl)methoxycyclohexyl)-1-butene [Compoundexpressed by general formula I wherein R¹ represents ethyl group, ringA¹ represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0, n2 is0, n3 is 1, R² represents a group expressed by formula II, and Xrepresents hydrogen atom (Compound No. 172)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that3-(trans-4-(4-ethylphenyl)methoxycyclohexyl)propanal was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 173 to 188) are synthesized.

173 1-cyano-4-(trans-4-(4-propylphenyl)methoxycyclohexyl)-1-butene

174 1-cyano-4-(trans-4-(4-butylphenyl)methoxycyclohexyl)-1-butene

175 1-cyano-4-(trans-4-(4-pentylphenyl)methoxycyclohexyl)-1-butene

1761-cyano-4-(trans-4-(trans-4-propylcyclohexyl)methoxycyclohexyl)-1-butene

1771-cyano-4-(trans-4-(trans-4-butylcyclohexyl)methoxycyclohexyl)-1-butene

1781-cyano-4-(trans-4-(trans-4-pentylcyclohexyl)methoxycyclohexyl)-1-butene

1791-cyano-4-(trans-4-(trans-4-heptylcyclohexyl)methoxycyclohexyl)-1-butene

1801-cyano-4-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)methoxycyclohexyl)-1-butene

1811-cyano-4-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)methoxycyclohexyl)-1-butene

1821-cyano-4-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)methoxycyclohexyl)-1-butene

1831-cyano-4-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)methoxycyclohexyl)-1-butene

1841-cyano-4-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)oxymethylcyclohexyl)-1-butene

1851-cyano-4-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)oxymethylcyclohexyl)-1-butene

1861-cyano-4-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)oxymethylcyclohexyl)-1-butene

1871-cyano-4-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)oxymethylcyclohexyl)-1-butene

1881-cyano-4-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)oxymethylcyclohexyl)-1-butene

EXAMPLE 12

Preparation of1-cyano-4-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents ethylgroup, ring A¹ represents 1,4-phenylene, B¹ represents 1,4-butylene, n1is 0, n2 is 0, n3 is 1, R² represents a group expressed by formula II,and X represents hydrogen atom (Compound No. 189)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that3-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)propanal was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 190 to 200) are synthesized.

190 1-cyano-4-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)-1-butene

191 1-cyano-4-(trans-4-(4-(4-butylphenyl)butyl)cyclohexyl)-1-butene

192 1-cyano-4-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)-1-butene

1931-cyano-4-(trans-4-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

1941-cyano-4-(trans-4-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

1951-cyano-4-(trans-4-(trans-4-(4-(4-butylphenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

1961-cyano-4-(trans-4-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

1971-cyano-4-(trans-4-(4-(trans-4-(4-ethylphenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

1981-cyano-4-(trans-4-(4-(trans-4-(4-propylphenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

1991-cyano-4-(trans-4-(4-(trans-4-(4-butylphenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

2001-cyano-4-(trans-4-(4-(trans-4-(4-pentylphenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

EXAMPLE 13

Preparation of1-cyano-4-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, ring A¹ represents 1,4-cyclohexylene, B¹ represents a covalentbond, n1 is 0, n2 is 0, n3 is 0, R² represents a group expressed byformula III, and X represents hydrogen atom (Compound No. 201)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-propenal was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

NI 191.7° C.

CN 45.3 to 45.9° C.

The starting material was prepared by the following method:

In 20 ml of THF (tetrahydrofuran), was suspended 5.0 g of1,3-dioxane-2-ylethyltriphenyl phosphonium bromide, and then 1.2 g ofpotassium butoxide was added portionwise thereto while stirring under acooled condition with ice. After the yellow suspension thus obtained wasstirred for 30 min, a solution prepared by dissolving 1.5 g oftrans-4-(trans-4-ethylcyclohexyl)cyclohexanone in 10 ml of THF was addeddropwise thereto. The reaction solution was stirred for 30 min under acooled condition with ice, the temperature of the solution was raised upto room temperature, and then the solution was passed through a shortcolumn filled with a silica gel, and concentrated under a reducedpressure. The yellow oily product thus obtained was purified by using asilica gel column chromatography to obtain 1.3 g of colorless crystal.As a result of analysis by various methods, this product was confirmedto be1,3-dioxane-2-ylethylidene-trans-4-(trans-4-ethylcyclohexyl)cyclohexane.

In a mixed solution comprising 50 ml of THF and 5 ml of 1N hydrochloricacid, was dissolved 1.3 of the compound, and the solution was stirredunder a reflux for 2 hours. After finishing of the reaction, thesolution was extracted with ether, and the organic layer was washed withwater, dried, and concentrated under a reduced pressure to obtain alight-yellow oily product. As a result of analysis by various methods,this product was confirmed to be3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl-2-propenal. This productwas used, without any purification, in the succeeding reaction.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 202 to 210) are synthesized.

2021-cyano-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)-1,3-butadiene

NI 213.7° C.

CN 75.2 to 74.9° C.

2031-cyano-4-(trans-4-(trans-4-butylcyclohexyl)cyclohexyl)-1,3-butadiene

2041-cyano-4-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)-1,3-butadiene

NI 209.7° C.

S_(B) N 67.8 to 68.3° C.

CS_(B) 64.1 to 64.7° C.

2051-cyano-4-(trans-4-(trans-4-heptylcyclohexyl)cyclohexyl)-1,3-butadiene

2061-cyano-4-(trans-4-(2-(trans-4-ethylcyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

2071-cyano-4-(trans-4-(2-(trans-4-propylcyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

2081-cyano-4-(trans-4-(2-(trans-4-butylcyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

2091-cyano-4-(trans-4-(2-(trans-4-pentylcyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

2101-cyano-4-(trans-4-(2-(trans-4-heptylcyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

EXAMPLE 14

Preparation of1-cyano-4-(trans-4-(4-ethylphenyl)cyclohexyl)-1,3-butadiene [Compoundexpressed by general formula I wherein R¹ represents ethyl group, ringA¹ represents 1,4-phenylene, B¹ represents a covalent bond, n1 is 0, n2is 0, n3 is 0, R² represents a group expressed by formula III, and Xrepresents hydrogen atom (Compound No. 211)]

Subject compound was synthesized by the same procedures as in Example 13with the exception that 3-(trans-4-(4-ethylphenyl)cyclohexyl)-2-propenalsynthesized from trans-4-(4-ethylphenyl)cyclohexanone was used asstarting material instead of3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-propenal.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 212 to 230) are synthesized.

212 1-cyano-4-(trans-4-(4-propylphenyl)cyclohexyl)-1,3-butadiene

213 1-cyano-4-(trans-4-(4-butylphenyl)cyclohexyl)-1,3-butadiene

214 1-cyano-4-(trans-4-(4-pentylphenyl)cyclohexyl)-1,3-butadiene

215 1-cyano-4-(trans-4-(4-heptylphenyl)cyclohexyl)-1,3-butadiene

216 1-cyano-4-(trans-4-(2-(4-ethylphenyl)ethyl)cyclohexyl)-1,3-butadiene

2171-cyano-4-(trans-4-(2-(4-propylphenyl)ethyl)cyclohexyl)-1,3-butadiene

218 1-cyano-4-(trans-4-(2-(4-butylphenyl)ethyl)cyclohexyl)-1,3-butadiene

2191-cyano-4-(trans-4-(2-(4-pentylphenyl)ethyl)cyclohexyl)-1,3-butadiene

2201-cyano-4-(trans-4-(2-(4-heptylphenyl)ethyl)cyclohexyl)-1,3-butadiene

2211-cyano-4-(trans-4-(trans-4-(4-methylphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

NI >300° C.

CN 104.2° C.

2221-cyano-4-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

2231-cyano-4-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

2241-cyano-4-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

2251-cyano-4-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

2261-cyano-4-(trans-4-(2-(trans-4-(4-ethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

2271-cyano-4-(trans-4-(2-(trans-4-(4-propylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

2281-cyano-4-(trans-4-(2-(trans-4-(4-butylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

2291-cyano-4-(trans-4-(2-(trans-4-(4-pentylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

2301-cyano-4-(trans-4-(2-(trans-4-(4-heptylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

EXAMPLE 15

Preparation of1-cyano-4-(trans-4-(2-(4-ethylcyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, ring A¹ represents 1,4-cyclohexylene, B¹ represents ethenylene,n1 is 0, n2 is 0, n3 is 0, R² represents a group expressed by formulaIII, and X represents hydrogen atom (Compound No. 231)]

Subject compound was synthesized by the same procedures as in Example 13with the exception that3-(trans-4-(2E-(trans-4-ethylcyclohexyl)ethenyl)cyclohexyl)-2-propenalsynthesized from(trans-4-(2E-(trans-4-ethylcyclohexyl)ethenyl)cyclohexanone was used asstarting material instead of3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-propenal.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 232 to 240) are synthesized.

2321-cyano-4-(trans-4-(2E-(trans-4-propylcyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

2331-cyano-4-(trans-4-(2E-(trans-4-butylcyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

2341-cyano-4-(trans-4-(2E-(trans-4-pentylcyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

2351-cyano-4-(trans-4-(2E-(trans-4-heptylcyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

2361-cyano-4-(trans-4-(2E-(trans-4-(4-ethylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

2371-cyano-4-(trans-4-(2E-(trans-4-(4-propylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

2381-cyano-4-(trans-4-(2E-(trans-4-(4-butylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

2391-cyano-4-(trans-4-(2E-(trans-4-(4-pentylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

2401-cyano-4-(trans-4-(2E-(trans-4-(4-heptylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

EXAMPLE 16

Preparation of trans-4-(4-cyano-1,3-butadienyl)cyclohexyltrans-4-ethylcyclohexane carboxylate [Compound expressed by generalformula I wherein R¹ represents ethyl group, ring A¹ represents1,4-cyclohexylene, B¹ represents carbonyloxy, n1 is 0, n2 is 0, n3 is 0,R² represents a group expressed by formula III, and X representshydrogen atom (Compound No. 241)]

Subject compound was synthesized by the same procedures as in Example 13with the exception that trans-4-(2-formylethenyl)cyclohexyltrans-4-ethylcyclohexane carboxylate synthesized from 4-oxocyclohexyltrans-4-ethylcyclohexane carboxylate was used as starting materialinstead of 3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-propenal.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 242 to 271) are synthesized.

242 trans-4-(4-cyano-1,3-butadienyl)cyclohexyl trans-4-propylcyclohexanecarboxylate

243 trans-4-(4-cyano-1,3-butadienyl)cyclohexyl trans-4-butylcyclohexanecarboxylate

244 trans-4-(4-cyano-1,3-butadienyl)cyclohexyl trans-4-pentylcyclohexanecarboxylate

245 trans-4-(4-cyano-1,3-butadienyl)cyclohexyl trans-4-hexylcyclohexanecarboxylate

246 trans-4-ethylcyclohexyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

247 trans-4-propylcyclohexyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

248 trans-4-butylcyclohexyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

249 trans-4-pentylcyclohexyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

250 trans-4-hexylcyclohexyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

251 trans-4-(4-cyano-1,3-butadienyl)cyclohexyl 4-ethyl benzoate

252 trans-4-(4-cyano-1,3-butadienyl)cyclohexyl 4-propyl benzoate

253 trans-4-(4-cyano-1,3-butadienyl)cyclohexyl 4-butyl benzoate

254 trans-4-(4-cyano-1,3-butadienyl)cyclohexyl 4-pentyl benzoate

255 trans-4-(4-cyano-1,3-butadienyl)cyclohexyl 4-hexyl benzoate

256 4-ethylphenyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

257 4-propylphenyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

258 4-butylphenyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

259 4-pentylphenyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

260 4-hexylphenyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

261 4-heptylphenyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

262 trans-4-(4-ethylphenyl)cyclohexyltrans-4-(4-cyano-1,3-butadienyl)cyclohexane carboxylate

263 trans-4-(4-propylphenyl)cyclohexyltrans-4-(4-cyano-1,3-butadienyl)cyclohexane carboxylate

264 trans-4-(4-butylphenyl)cyclohexyltrans-4-(4-cyano-1,3-butadienyl)cyclohexane carboxylate

265 trans-4-(4-pentylphenyl)cyclohexyltrans-4-(4-cyano-1,3-butadienyl)cyclohexane carboxylate

266 trans-4-(4-hexylphenyl)cyclohexyltrans-4-(4-cyano-1,3-butadienyl)cyclohexane carboxylate

267 trans-4-(4-cyano-1,3-butadienyl)cyclohexyltrans-4-(4-ethylphenyl)cyclohexane carboxylate

268 trans-4-(4-cyano-1,3-butadienyl)cyclohexyltrans-4-(4-propylphenyl)cyclohexane carboxylate

269 trans-4-(4-cyano-1,3-butadienyl)cyclohexyltrans-4-(4-butylphenyl)cyclohexane carboxylate

270 trans-4-(4-cyano-1,3-butadienyl)cyclohexyltrans-4-(4-pentylphenyl)cyclohexane carboxylate

271 trans-4-(4-cyano-1,3-butadienyl)cyclohexyltrans-4-(4-hexylphenyl)cyclohexane carboxylate

EXAMPLE 17

Preparation of1-cyano-4-(trans-4-(4-ethylphenyl)methoxycyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, ring A¹ represents 1,4-phenylene, B¹ represents methyleneoxy, n1is 0, n2 is 0, n3 is 0, R² represents a group expressed by formula III,and X represents hydrogen atom (Compound No. 272)]

Subject compound was synthesized by the same procedures as in Example 13with the exception that3-(trans-4-(4-ethylphenyl)methoxycyclohexyl)-2-propenal synthesized from(trans-4-(4-ethylphenyl)methoxycyclohexanone was used as startingmaterial instead of3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-propenal.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 273 to 287) are synthesized.

273 1-cyano-4-(trans-4-(4-propylphenyl)methoxycyclohexyl)-1,3-butadiene

274 1-cyano-4-(trans-4-(4-butylphenyl)methoxycyclohexyl)-1,3-butadiene

275 1-cyano-4-(trans-4-(4-pentylphenyl)methoxycyclohexyl)-1,3-butadiene

276 1-cyano-4-(trans-4-(4-heptylphenyl)methoxycyclohexyl)-1,3-butadiene

2771-cyano-4-(trans-4-(trans-4-propylcyclohexyl)methoxycyclohexyl)-1,3-butadiene

2781-cyano-4-(trans-4-(trans-4-butylcyclohexyl)methoxycyclohexyl)-1,3-butadiene

2791-cyano-4-(trans-4-(trans-4-pentylcyclohexyl)methoxycyclohexyl)-1,3-butadiene

2801-cyano-4-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

2811-cyano-4-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

2821-cyano-4-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

2831-cyano-4-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

2841-cyano-4-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-butadiene

2851-cyano-4-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-butadiene

2861-cyano-4-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-butadiene

2871-cyano-4-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-butadiene

EXAMPLE 18

Preparation of1-cyano-4-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, ring A¹ represents 1,4-phenylene, B¹ represents butenylene, n1 is0, n2 is 0, n3 is 0, R² represents a group expressed by formula III, andX represents hydrogen atom (Compound No. 288)]

Subject compound was synthesized by the same procedures as in Example 13with the exception that3-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)-2-propenal synthesizedfrom trans-4-(4-(4-ethylphenyl)butyl)cyclohexanone was used as startingmaterial instead of3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-propenal.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 289 to 300) are synthesized.

2891-cyano-4-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)-1,3-butadiene

290 1-cyano-4-(trans-4-(4-(4-butylphenyl)butyl)cyclohexyl)-1,3-butadiene

2911-cyano-4-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)-1,3-butadiene

2921-cyano-4-(trans-4-(4-(4-heptylphenyl)butyl)cyclohexyl)-1,3-butadiene

2931-cyano-4-(trans-4-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

2941-cyano-4-(trans-4-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

2951-cyano-4-(trans-4-(trans-4-(4-(4-butylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

2961-cyano-4-(trans-4-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

2971-cyano-4-(trans-4-(4-(trans-4-(4-ethylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-butadiene

2981-cyano-4-(trans-4-(4-(trans-4-(4-propylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-butadiene

2991-cyano-4-(trans-4-(4-(trans-4-pentylcyclohexyl)butyl)cyclohexyl)-1,3-butadiene

3001-cyano-4-(trans-4-(4-(trans-4-heptylcyclohexyl)butyl)cyclohexyl)-1,3-butadiene

EXAMPLE 19

Preparation of1-cyano-6-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, ring A¹ represents 1,4-cyclohexylene, B¹ represents a covalentbond, n1 is 0, n2 is 0, n3 is 1, R² represents a group expressed byformula III, and X represents hydrogen atom (Compound No. 301)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that5-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-pentene-1-al was usedas starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

NI 191.7° C.

CN 45.3 to 45.9° C.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 302 to 310) are synthesized.

3021-cyano-6-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)-1,3-hexadiene

3031-cyano-6-(trans-4-(trans-4-butylcyclohexyl)cyclohexyl)-1,3-hexadiene

3041-cyano-6-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)-1,3-hexadiene

3051-cyano-6-(trans-4-(trans-4-heptylcyclohexyl)cyclohexyl)-1,3-hexadiene

3061-cyano-6-(trans-4-(2-(trans-4-ethylcyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

3071-cyano-6-(trans-4-(2-(trans-4-propylcyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

3081-cyano-6-(trans-4-(2-(trans-4-butylcyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

3091-cyano-6-(trans-4-(2-(trans-4-pentylcyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

3101-cyano-6-(trans-4-(2-(trans-4-heptylcyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 20

Preparation of1-cyano-6-(trans-4-(4-ethylphenyl)cyclohexyl)-1,3-hexadiene [Compoundexpressed by general formula I wherein R¹ represents ethyl group, ringA¹ represents 1,4-phenylene, B¹ represents a covalent bond, n1 is 0, n2is 0, n3 is 1, R² represents a group expressed by formula III, and Xrepresents hydrogen atom (Compound No. 311)]

Subject compound was synthesized by the same procedures as in Example 13with the exception that5-(trans-4-(4-ethylphenyl)cyclohexyl)-2-pentene-1-al synthesized fromtrans-4-(4-ethylphenyl)cyclohexanone was used as starting materialinstead of 3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-propenal.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 312 to 330) are synthesized.

312 1-cyano-6-(trans-4-(4-propylphenyl)cyclohexyl)-1,3-hexadiene

313 1-cyano-6-(trans-4-(4-butylphenyl)cyclohexyl)-1,3-hexadiene

314 1-cyano-6-(trans-4-(4-pentylphenyl)cyclohexyl)-1,3-hexadiene

315 1-cyano-6-(trans-4-(4-heptylphenyl)cyclohexyl)-1,3-hexadiene

316 1-cyano-6-(trans-4-(2-(4-ethylphenyl)ethyl)cyclohexyl)-1,3-hexadiene

3171-cyano-6-(trans-4-(2-(4-propylphenyl)ethyl)cyclohexyl)-1,3-hexadiene

318 1-cyano-6-(trans-4-(2-(4-butylphenyl)ethyl)cyclohexyl)-1,3-hexadiene

3191-cyano-6-(trans-4-(2-(4-pentylphenyl)ethyl)cyclohexyl)-1,3-hexadiene

3201-cyano-6-(trans-4-(2-(4-heptylphenyl)ethyl)cyclohexyl)-1,3-hexadiene

3211-cyano-6-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

3221-cyano-6-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

3231-cyano-6-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

3241-cyano-6-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

3251-cyano-6-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

3261-cyano-6-(trans-4-(2-(trans-4-(4-ethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

3271-cyano-6-(trans-4-(2-(trans-4-(4-propylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

3281-cyano-6-(trans-4-(2-(trans-4-(4-butylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

3291-cyano-6-(trans-4-(2-(trans-4-(4-pentylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

3301-cyano-6-(trans-4-(2-(trans-4-(4-heptylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 21

Preparation of1-cyano-6-(trans-4-(2-(trans-4-ethylcyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, ring A¹ represents 1,4-cyclohexylene, B¹ represents ethenylene,n1 is 0, n2 is 0, n3 is 1, R² represents a group expressed by formulaIII, and X represents hydrogen atom (Compound No. 331)]

Subject compound was synthesized by the same procedures as in Example 13with the exception that5-(trans-4-(2E-(trans-4-ethylcyclohexyl)ethenyl)cyclohexyl)-2-pentene-1-alsynthesized fromtrans-4-(2E-(trans-4-ethylcyclohexyl)ethenyl)cyclohexanone was used asstarting material instead of3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-propenal.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 332 to 340) are synthesized.

3321-cyano-6-(trans-4-(2E-(trans-4-propylcyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

3331-cyano-6-(trans-4-(2E-(trans-4-butylcyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

3341-cyano-6-(trans-4-(2E-(trans-4-pentylcyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

3351-cyano-6-(trans-4-(2E-(trans-4-heptylcyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

3361-cyano-6-(trans-4-(2E-(trans-4-(4-ethylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

3371-cyano-6-(trans-4-(2E-(trans-4-(4-propylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

3381-cyano-6-(trans-4-(2E-(trans-4-(4-butylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

3391-cyano-6-(trans-4-(2E-(trans-4-(4-pentylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

3401-cyano-6-(trans-4-(2E-(trans-4-(4-heptylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 22

Preparation of trans-4-(6-cyano-3,5-hexadienyl)cyclohexyltrans-4-ethylcyclohexane carboxylate [Compound expressed by generalformula I wherein R¹ represents ethyl group, ring A¹ represents1,4-cyclohexylene, B¹ represents carbonyloxy, n1 is 0, n2 is 0, n3 is 1,R² represents a group expressed by formula III, and X representshydrogen atom (Compound No. 341)]

Subject compound was synthesized by the same procedures as in Example 13with the exception that trans-4-(4-formyl-3-butenyl)cyclohexyltrans-4-ethylcyclohexane carboxylate was used as starting materialinstead of 3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-propenal.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 342 to 371) are synthesized.

342 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl trans-4-propylcyclohexanecarboxylate

343 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl trans-4-butylcyclohexanecarboxylate

344 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl trans-4-pentylcyclohexanecarboxylate

345 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl trans-4-hexylcyclohexanecarboxylate

346 trans-4-ethylcyclohexyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

347 trans-4-propylcyclohexyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

348 trans-4-butylcyclohexyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

349 trans-4-pentylcyclohexyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

350 trans-4-hexylcyclohexyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

351 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl 4-ethyl benzoate

352 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl 4-propyl benzoate

353 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl 4-butyl benzoate

354 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl 4-pentyl benzoate

355 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl 4-hexyl benzoate

356 4-ethylphenyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

357 4-propylphenyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

358 4-butylphenyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

359 4-pentylphenyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

360 4-hexylphenyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

361 4-heptylphenyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

362 trans-4-(4-ethylphenyl)cyclohexyltrans-4-(6-cyano-3,5-hexadienyl)cyclohexane carboxylate

363 trans-4-(4-propylphenyl)cyclohexyltrans-4-(6-cyano-3,5-hexadienyl)cyclohexane carboxylate

364 trans-4-(4-butylphenyl)cyclohexyltrans-4-(6-cyano-3,5-hexadienyl)cyclohexane carboxylate

365 trans-4-(4-pentylphenyl)cyclohexyltrans-4-(6-cyano-3,5-hexadienyl)cyclohexane carboxylate

366 trans-4-(4-hexylphenyl)cyclohexyltrans-4-(6-cyano-3,5-hexadienyl)cyclohexane carboxylate

367 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyltrans-4-(4-ethylphenyl)cyclohexane carboxylate

368 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyltrans-4-(4-propylphenyl)cyclohexane carboxylate

369 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyltrans-4-(4-butylphenyl)cyclohexane carboxylate

370 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyltrans-4-(4-pentylphenyl)cyclohexane carboxylate

371 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyltrans-4-(4-hexylphenyl)cyclohexane carboxylate

EXAMPLE 23

Preparation of1-cyano-6-(trans-4-(4-ethylphenyl)methoxycyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, ring A¹ represents 1,4-phenylene, B¹ represents methyleneoxy, n1is 0, n2 is 0, n3 is 1, R² represents a group expressed by formula III,and X represents hydrogen atom (Compound No. 372)]

Subject compound was synthesized by the same procedures as in Example 13with the exception that5-(trans-4-(4-ethylphenyl)methoxycylohexyl)-2-pentene-1-al synthesizedfrom trans-4-(4-ethylphenyl)methoxycyclohexanone was used as startingmaterial instead of3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-propenal.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 373 to 387) are synthesized.

373 1-cyano-6-(trans-4-(4-propylphenyl)methoxycyclohexyl-1,3-hexadiene

374 1-cyano-6-(trans-4-(4-butylphenyl)methoxycyclohexyl-1,3-hexadiene

375 1-cyano-6-(trans-4-(4-pentylphenyl)methoxycyclohexyl-1,3-hexadiene

376 1-cyano-6-(trans-4-(4-heptylphenyl)methoxycyclohexyl-1,3-hexadiene

3771-cyano-6-(trans-4-(trans-4-propylcyclohexyl)methoxycyclohexyl)-1,3-hexadiene

3781-cyano-6-(trans-4-(trans-4-butylcyclohexyl)methoxycyclohexyl)-1,3-hexadiene

3791-cyano-6-(trans-4-(trans-4-pentylcyclohexyl)methoxycyclohexyl)-1,3-hexadiene

3801-cyano-6-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

3811-cyano-6-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

3821-cyano-6-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

3831-cyano-6-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

3841-cyano-6-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-hexadiene

3851-cyano-6-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-hexadiene

3861-cyano-6-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-hexadiene

3871-cyano-6-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-hexadiene

EXAMPLE 24

Preparation of1-cyano-6-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, ring A¹ represents 1,4-phenylene, B¹ represents butenylene, n1 is0, n2 is 0, n3 is 1, R² represents a group expressed by formula III, andX represents hydrogen atom (Compound No. 388)]

Subject compound was synthesized by the same procedures as in Example 13with the exception that5-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)-2-pentene-1-alsynthesized from trans-4-(4-(4-ethylphenyl)butyl)cyclohexanone was usedas starting material instead of3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-propenal.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 389 to 400) are synthesized.

3891-cyano-6-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)-1,3-hexadiene

390 1-cyano-6-(trans-4-(4-(4-butylphenyl)butyl)cyclohexyl)-1,3-hexadiene

3911-cyano-6-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)-1,3-hexadiene

3921-cyano-6-(trans-4-(4-(4-heptylphenyl)butyl)cyclohexyl)-1,3-hexadiene

3931-cyano-6-(trans-4-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

3941-cyano-6-(trans-4-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

3951-cyano-6-(trans-4-(trans-4-(4-(4-butylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

3961-cyano-6-(trans-4-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

3971-cyano-6-(trans-4-(4-(trans-4-(4-ethylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

3981-cyano-6-(trans-4-(4-(trans-4-(4-propylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

3991-cyano-6-(trans-4-(4-(trans-4-pentylcyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

4001-cyano-6-(trans-4-(4-(trans-4-heptylcyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 25

Preparation of1-fluoro-1-cyano-2-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)ethene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-cyclohexylene, B¹ represents a covalent bond,n1 is 0, n2 is 0, n3 is 0, R² represents a group expressed by formulaII, and X represents fluorine atom (Compound No. 401)]

A solution of tribromofluoromethane and triphenyl phosphine in ethyleneglycol dimethyl ether was stirred at 70° C. for 1 hour. The reactionsolution was cooled with ice, and a solution oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde intetrahydrofuran was added thereto. After the reaction solution wasfurther stirred for 1 hour, the temperature of the solution wasgradually raised up to room temperature, and insoluble substances wereremoved by filtration. Dilute hydrochloric acid was added to thefiltrate, and it was extracted with toluene. After the organic layer waswashed with water, it was dried by using anhydrous magnesium sulfate,and concentrated under a reduced pressure to obtain a brown oilyproduct. After this product was purified by using a silica gel columnchromatography, it was recrystallized from heptane to obtaintrans-4-(trans-4-ethylcyclohexyl)cyclohexyl-2-fluoro-2-bromoethene.

The compound and copper cyanide were dissolved in 2-methylpyrrolidone,and refluxed for 3 hours. The reaction solution was cooled down to roomtemperature, a dilute hydrochloric acid solution of iron chloride wasadded thereto, and then the solution was extracted with ethyl acetate.The organic layer thus obtained was washed with water, dried overanhydrous magnesium sulfate, and concentrated under a reduced pressureto obtain brown oily product. After this product was purified by using asilica gel column chromatography, it was recrystallized from toluene toobtain the subject compound.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 402 to 410) are synthesized.

4021-fluoro-1-cyano-2-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)ethene

NI 124.8° C.

S_(B) N 66.0° C.

CS_(B) lower than 15° C.

4031-fluoro-1-cyano-2-(trans-4-(trans-4-butylcyclohexyl)cyclohexyl)ethene

NI 121.9° C.

S_(B) N 74.8° C.

CS_(B) lower than 15° C.

4041-fluoro-1-cyano-2-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)ethene

NI 119.3° C.

S_(B) N 68.5° C.

CS_(B) lower than 15° C.

4051-fluoro-1-cyano-2-(trans-4-(trans-4-heptylcyclohexyl)cyclohexyl)ethene

4061-fluoro-1-cyano-2-(trans-4-(2-(trans-4-ethylcyclohexyl)ethyl)cyclohexyl)ethene

4071-fluoro-1-cyano-2-(trans-4-(2-(trans-4-propylcyclohexyl)ethyl)cyclohexyl)ethene

4081-fluoro-1-cyano-2-(trans-4-(2-(trans-4-butylcyclohexyl)ethyl)cyclohexyl)ethene

4091-fluoro-1-cyano-2-(trans-4-(2-(trans-4-pentylcyclohexyl)ethyl)cyclohexyl)ethene

4101-fluoro-1-cyano-2-(trans-4-(2-(trans-4-heptylcyclohexyl)ethyl)cyclohexyl)ethene

EXAMPLE 26

Preparation of1-fluoro-1-cyano-2-(trans-4-(4-ethylphenyl)cyclohexyl)ethene [Compoundexpressed by general formula I wherein R¹ represents ethyl group, A¹represents 1,4-phenylene, B¹ represents a covalent bond, n1 is 0, n2 is0, n3 is 0, R² represents a group expressed by formula II, and Xrepresents fluorine atom (Compound No. 411)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that trans-4-(4-ethylphenyl)cyclohexane carboaldehydewas used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 412 to 430) are synthesized.

412 1-fluoro-1-cyano-2-(trans-4-(4-propylphenyl)cyclohexyl)ethene

413 1-fluoro-1-cyano-2-(trans-4-(4-butylphenyl)cyclohexyl)ethene

414 1-fluoro-1-cyano-2-(trans-4-(4-pentylphenyl)cyclohexyl)ethene

415 1-fluoro-1-cyano-2-(trans-4-(4-heptylphenyl)cyclohexyl)ethene

4161-fluoro-1-cyano-2-(trans-4-(2-(4-ethylphenyl)ethyl)cyclohexyl)ethene

4171-fluoro-1-cyano-2-(trans-4-(2-(4-propylphenyl)ethyl)cyclohexyl)ethene

4181-fluoro-1-cyano-2-(trans-4-(2-(4-butylphenyl)ethyl)cyclohexyl)ethene

4191-fluoro-1-cyano-2-(trans-4-(2-(4-pentylphenyl)ethyl)cyclohexyl)ethene

420 1-fluoro-1-cyano-2-(trans-4-(4-methylbiphenyl)cyclohexyl)ethene

NI 251° C.

S_(A) N 171.3° C.

CS_(A) 134.7° C.

CC' 111.7° C.

4211-fluoro-1-cyano-2-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)cyclohexyl)ethene

NI 216.8° C.

CN 115.0° C.

4221-fluoro-1-cyano-2-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)cyclohexyl)ethene

4231-fluoro-1-cyano-2-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)cyclohexyl)ethene

4241-fluoro-1-cyano-2-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)cyclohexyl)ethene

4251-fluoro-1-cyano-2-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)cyclohexyl)ethene

4261-fluoro-1-cyano-2-(trans-4-(2-(trans-4-(4-ethylphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

4271-fluoro-1-cyano-2-(trans-4-(2-(trans-4-(4-propylphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

4281-fluoro-1-cyano-2-(trans-4-(2-(trans-4-(4-butylphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

4291-fluoro-1-cyano-2-(trans-4-(2-(trans-4-(4-pentylphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

4301-fluoro-1-cyano-2-(trans-4-(2-(trans-4-(4-heptylphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

EXAMPLE 27

Preparation of1-fluoro-1-cyano-2-(trans-4-(2-(trans-4-ethylcyclohexyl)ethenyl)cyclohexyl)ethene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-cyclohexylene, B¹ represents 1,2-ethenylene, n1is 0, n2 is 0, n3 is 0, R² represents a group expressed by formula II,and X represents fluorine atom (Compound No. 431)]

Subject compound was synthesized by the same procedures as in Example 1with the exception thattrans-4-(2E-(trans-4-ethylcyclohexyl)ethenyl)cyclohexane carboaldehydewas used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 432 to 440) are synthesized.

4321-fluoro-1-cyano-2-(trans-4-(2E-(trans-4-propylcyclohexyl)ethenyl)cyclohexyl)ethene

4331-fluoro-1-cyano-2-(trans-4-(2E-(trans-4-butylcyclohexyl)ethenyl)cyclohexyl)ethene

4341-fluoro-1-cyano-2-(trans-4-(2E-(trans-4-pentylcyclohexyl)ethenyl)cyclohexyl)ethene

4351-fluoro-1-cyano-2-(trans-4-(2E-(trans-4-heptylcyclohexyl)ethenyl)cyclohexyl)ethene

4361-fluoro-1-cyano-2-(trans-4-(2E-(trans-4-(4-ethylphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

4371-fluoro-1-cyano-2-(trans-4-(2E-(trans-4-(4-propylphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

4381-fluoro-1-cyano-2-(trans-4-(2E-(trans-4-(4-butylphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

4391-fluoro-1-cyano-2-(trans-4-(2E-(trans-4-(4-pentylphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

4401-fluoro-1-cyano-2-(trans-4-(2E-(trans-4-(4-heptylphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

EXAMPLE 28

Preparation of trans-4-(2-cyano-2-fluoroethenyl)cyclohexyltrans-4-ethylcyclohexane carboxylate [Compound expressed by generalformula I wherein R¹ represents ethyl group, A¹ represents1,4-cyclohexylene, B¹ represents carbonyloxy, n1 is 0, n2 is 0, n3 is 0,R² represents a group expressed by formula II, and X represents fluorineatom (Compound No. 441)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-formylcyclohexyltrans-4-ethylcyclohexane carboxylate was used as starting materialinstead of trans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 442 to 471) are synthesized.

442 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyltrans-4-propylcyclohexane carboxylate

443 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyl trans-4-butylcyclohexanecarboxylate

444 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyltrans-4-pentylcyclohexane carboxylate

445 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyl trans-4-hexylcyclohexanecarboxylate

446 trans-4-ethylcyclohexyl trans-4-(2-cyano-2-fluoroethenyl)cyclohexanecarboxylate

447 trans-4-propylcyclohexyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

448 trans-4-butylcyclohexyl trans-4-(2-cyano-2-fluoroethenyl)cyclohexanecarboxylate

449 trans-4-pentylcyclohexyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

450 trans-4-hexylcyclohexyl trans-4-(2-cyano-2-fluoroethenyl)cyclohexanecarboxylate

451 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyl 4-ethyl benzoate

452 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyl 4-propyl benzoate

453 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyl 4-butyl benzoate

454 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyl 4-pentyl benzoate

455 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyl 4-hexyl benzoate

456 4-ethylphenyl trans-4-(2-cyano-2-fluoroethenyl)cyclohexanecarboxylate

457 4-propylphenyl trans-4-(2-cyano-2-fluoroethenyl)cyclohexanecarboxylate

458 4-butylphenyl trans-4-(2-cyano-2-fluoroethenyl)cyclohexanecarboxylate

459 4-pentylphenyl trans-4-(2-cyano-2-fluoroethenyl)cyclohexanecarboxylate

460 4-hexylphenyl trans-4-(2-cyano-2-fluoroethenyl)cyclohexanecarboxylate

461 4-heptylphenyl trans-4-(2-cyano-2-fluoroethenyl)cyclohexanecarboxylate

462 trans-4-(4-ethylphenyl)cyclohexyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

463 trans-4-(4-propylphenyl)cyclohexyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

464 trans-4-(4-butylphenyl)cyclohexyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

465 trans-4-(4-pentylphenyl)cyclohexyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

466 trans-4-(4-hexylphenyl)cyclohexyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

467 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyltrans-4-(4-ethylphenyl)cyclohexane carboxylate

468 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyltrans-4-(4-propylphenyl)cyclohexane carboxylate

469 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyltrans-4-(4-butylphenyl)cyclohexane carboxylate

470 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyltrans-4-(4-pentylphenyl)cyclohexane carboxylate

471 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyltrans-4-(4-hexylphenyl)cyclohexane carboxylate

EXAMPLE 29

Preparation of1-fluoro-1-cyano-2-(trans-4-(4-ethylphenyl)methoxycyclohexyl)ethene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0,n2 is 0, n3 is 0, R² represents a group expressed by formula II, and Xrepresents fluorine atom (Compound No. 472)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(4-ethylphenyl)methoxycyclohexanecarboaldehyde was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 473 to 489) are synthesized.

473 1-fluoro-1-cyano-2-(trans-4-(4-propylphenyl)methoxycyclohexyl)ethene

474 1-fluoro-1-cyano-2-(trans-4-(4-butylphenyl)methoxycyclohexyl)ethene

475 1-fluoro-1-cyano-2-(trans-4-(4-pentylphenyl)methoxycyclohexyl)ethene

476 1-fluoro-1-cyano-2-(trans-4-(4-heptylphenyl)methoxycyclohexyl)ethene

4771-fluoro-1-cyano-2-(trans-4-(trans-4-propylcyclohexyl)methoxycyclohexyl)ethene

4781-fluoro-1-cyano-2-(trans-4-(trans-4-butylcyclohexyl)methoxycyclohexyl)ethene

4791-fluoro-1-cyano-2-(trans-4-(trans-4-pentylcyclohexyl)methoxycyclohexyl)ethene

4801-fluoro-1-cyano-2-(trans-4-(trans-4-heptylcyclohexyl)methoxycyclohexyl)ethene

4811-fluoro-1-cyano-2-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)methoxycyclohexyl)ethene

4821-fluoro-1-cyano-2-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)methoxycyclohexyl)ethene

4831-fluoro-1-cyano-2-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)methoxycyclohexyl)ethene

4841-fluoro-1-cyano-2-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)methoxycyclohexyl)ethene

4851-fluoro-1-cyano-2-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)methoxycyclohexyl)ethene

4861-fluoro-1-cyano-2-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)oxymethylcyclohexyl)ethene

4871-fluoro-1-cyano-2-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)oxymethylcyclohexyl)ethene

4881-fluoro-1-cyano-2-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)oxymethylcyclohexyl)ethene

4891-fluoro-1-cyano-2-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)oxymethylcyclohexyl)ethene

EXAMPLE 30

Preparation of1-fluoro-1-cyano-2-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)ethene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-phenylene, B¹ represents 1,4-butylene, n1 is 0,n2 is 0, n3 is 0, R² represents a group expressed by formula II, and xrepresents fluorine atom (Compound No. 490)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(4-(4-ethylphenyl)butyl)cyclohexanecarboaldehyde was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 491 to 500) are synthesized.

4911-fluoro-1-cyano-2-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)ethene

4921-fluoro-1-cyano-2-(trans-4-(4-(4-butylphenyl)butyl)cyclohexyl)ethene

4931-fluoro-1-cyano-2-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)ethene

4941-fluoro-1-cyano-2-(trans-4-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)cyclohexyl)ethene

4951-fluoro-1-cyano-2-(trans-4-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)cyclohexyl)ethene

4961-fluoro-1-cyano-2-(trans-4-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)cyclohexyl)ethene

4971-fluoro-1-cyano-2-(trans-4-(trans-4-(4-(4-heptylphenyl)butyl)cyclohexyl)cyclohexyl)ethene

4981-fluoro-1-cyano-2-(trans-4-(4-(trans-4-(4-ethylphenyl)cyclohexyl)butyl)cyclohexyl)ethene

4991-fluoro-1-cyano-2-(trans-4-(4-(trans-4-(4-propylphenyl)cyclohexyl)butyl)cyclohexyl)ethene

5001-fluoro-1-cyano-2-(trans-4-(4-(trans-4-(4-butylphenyl)cyclohexyl)butyl)cyclohexyl)ethene

EXAMPLE 31

Preparation of1-cyano-1-fluoro-4-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-cyclohexylene, B¹ represents a covalent bond,n1 is 0, n2 is 0, n3 is 1, R² represents a group expressed by formulaII, and X represents fluorine atom (Compound No. 501)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)propanal was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 502 to 510) are synthesized.

5021-cyano-1-fluoro-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)-1-butene

5031-cyano-1-fluoro-4-(trans-4-(trans-4-butylcyclohexyl)cyclohexyl)-1-butene

5041-cyano-1-fluoro-4-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)-1-butene

5051-cyano-1-fluoro-4-(trans-4-(trans-4-heptylcyclohexyl)cyclohexyl)-1-butene

5061-cyano-1-fluoro-4-(trans-4-(2-(trans-4-ethylcyclohexyl)ethyl)cyclohexyl)-1-butene

5071-cyano-1-fluoro-4-(trans-4-(2-(trans-4-propylcyclohexyl)ethyl)cyclohexyl)-1-butene

5081-cyano-1-fluoro-4-(trans-4-(2-(trans-4-butylcyclohexyl)ethyl)cyclohexyl)-1-butene

5091-cyano-1-fluoro-4-(trans-4-(2-(trans-4-pentylcyclohexyl)ethyl)cyclohexyl)-1-butene

5101-cyano-1-fluoro-4-(trans-4-(2-(trans-4-heptylcyclohexyl)ethyl)cyclohexyl)-1-butene

EXAMPLE 32

Preparation of1-cyano-1-fluoro-4-(trans-4-(4-ethylphenyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, n1 is0, n2 is 0, n3 is 1, R² represents a group expressed by formula II, andX represents fluorine atom (Compound No. 511)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that 3-(trans-4-(4-ethylphenyl)cyclohexyl)propanalwas used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 512 to 530) are synthesized.

512 1-cyano-1-fluoro-4-(trans-4-(4-propylphenyl)cyclohexyl)-1-butene

513 1-cyano-1-fluoro-4-(trans-4-(4-butylphenyl)cyclohexyl)-1-butene

514 1-cyano-1-fluoro-4-(trans-4-(4-pentylphenyl)cyclohexyl)-1-butene

515 1-cyano-1-fluoro-4-(trans-4-(4-heptylphenyl)cyclohexyl)-1-butene

5161-cyano-1-fluoro-4-(trans-4-(2-(4-ethylphenyl)ethyl)cyclohexyl)-1-butene

5171-cyano-1-fluoro-4-(trans-4-(2-(4-propylphenyl)ethyl)cyclohexyl)-1-butene

5181-cyano-1-fluoro-4-(trans-4-(2-(4-butylphenyl)ethyl)cyclohexyl)-1-butene

5191-cyano-1-fluoro-4-(trans-4-(2-(4-pentylphenyl)ethyl)cyclohexyl)-1-butene

5201-cyano-1-fluoro-4-(trans-4-(2-(4-heptylphenyl)ethyl)cyclohexyl)-1-butene

5211-cyano-1-fluoro-4-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)cyclohexyl)-1-butene

5221-cyano-1-fluoro-4-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)cyclohexyl)-1-butene

5231-cyano-1-fluoro-4-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)cyclohexyl)-1-butene

5241-cyano-1-fluoro-4-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)cyclohexyl)-1-butene

5251-cyano-1-fluoro-4-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)cyclohexyl)-1-butene

5261-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-ethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

5271-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-propylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

5281-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-butylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

5291-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-pentylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

5301-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-heptylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

EXAMPLE 33

Preparation of1-cyano-1-fluoro-4-(trans-4-(2-(trans-4-ethylcyclohexyl)ethenyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-cyclohexylene, B¹ represents 1,2-ethenylene, n1is 0, n2 is 0, n3 is 1, R² represents a group expressed by formula II,and X represents fluorine atom (Compound No. 531)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that3-(trans-4-(2E-(trans-4-ethylcyclohexyl)ethenyl)cyclohexyl)propanal wasused as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 532 to 540) are synthesized.

5321-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-propylcyclohexyl)ethenyl)cyclohexyl)-1-butene

5331-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-butylcyclohexyl)ethenyl)cyclohexyl)-1-butene

5341-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-pentylcyclohexyl)ethenyl)cyclohexyl)-1-butene

5351-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-heptylcyclohexyl)ethenyl)cyclohexyl)-1-butene

5361-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-ethylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

5371-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-propylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

5381-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-butylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

5391-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-pentylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

5401-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-heptylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

EXAMPLE 34

Preparation of trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-ethylcyclohexane carboxylate [Compound expressed by generalformula I wherein R¹ represents ethyl group, A¹ represents1,4-cyclohexylene, B¹ represents carbonyloxy, n1 is 0, n2 is 0, n3 is 1,R² represents a group expressed by formula II, and X represents fluorineatom (Compound No. 541)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that trans-4-(2-formylethyl)cyclohexyltrans-4-ethylcyclohexane carboxylate was used as starting materialinstead of trans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 542 to 571) are synthesized.

542 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-propylcyclohexane carboxylate

543 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-butylcyclohexane carboxylate

544 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-pentylcyclohexane carboxylate

545 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-hexylcyclohexane carboxylate

546 trans-4-ethylcyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

547 trans-4-propylcyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

548 trans-4-butylcyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

549 trans-4-pentylcyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

550 trans-4-hexylcyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

551 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyl 4-ethyl benzoate

552 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyl 4-propyl benzoate

553 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyl 4-butyl benzoate

554 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyl 4-pentyl benzoate

555 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyl 4-hexyl benzoate

556 4-ethylphenyl trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexanecarboxylate

557 4-propylphenyl trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexanecarboxylate

558 4-butylphenyl trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexanecarboxylate

559 4-pentylphenyl trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexanecarboxylate

560 4-hexylphenyl trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexanecarboxylate

561 4-heptylphenyl trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexanecarboxylate

562 trans-4-(4-ethylphenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

563 trans-4-(4-propylphenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

564 trans-4-(4-butylphenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

565 trans-4-(4-pentylphenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

566 trans-4-(4-hexylphenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

567 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-(4-ethylphenyl)cyclohexane carboxylate

568 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-(4-propylphenyl)cyclohexane carboxylate

569 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-(4-butylphenyl)cyclohexane carboxylate

570 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-(4-pentylphenyl)cyclohexane carboxylate

571 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-(4-hexylphenyl)cyclohexane carboxylate

EXAMPLE 35

Preparation of1-cyano-1-fluoro-4-(trans-4-(4-ethylphenyl)methoxycyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0,n2 is 0, n3 is 1, R² represents a group expressed by formula II, and Xrepresents fluorine atom (Compound No. 572)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that3-(trans-4-(4-ethylphenyl)methoxycyclohexyl)propanal was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 573 to 589) are synthesized.

5731-cyano-1-fluoro-4-(trans-4-(4-propylphenyl)methoxycyclohexyl)-1-butene

5741-cyano-1-fluoro-4-(trans-4-(4-butylphenyl)methoxycyclohexyl)-1-butene

5751-cyano-1-fluoro-4-(trans-4-(4-pentylphenyl)methoxycyclohexyl)-1-butene

5761-cyano-1-fluoro-4-(trans-4-(4-heptylphenyl)methoxycyclohexyl)-1-butene

5771-cyano-1-fluoro-4-(trans-4-(trans-4-propylcyclohexyl)methoxycyclohexyl)-1-butene

5781-cyano-1-fluoro-4-(trans-4-(trans-4-butylcyclohexyl)methoxycyclohexyl)-1-butene

5791-cyano-1-fluoro-4-(trans-4-(trans-4-pentylcyclohexyl)methoxycyclohexyl)-1-butene

5801-cyano-1-fluoro-4-(trans-4-(trans-4-heptylcyclohexyl)methoxycyclohexyl)-1-butene

5811-cyano-1-fluoro-4-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)methoxycyclohexyl)-1-butene

5821-cyano-1-fluoro-4-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)methoxycyclohexyl)-1-butene

5831-cyano-1-fluoro-4-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)methoxycyclohexyl)-1-butene

5841-cyano-1-fluoro-4-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)methoxycyclohexyl)-1-butene

5851-cyano-1-fluoro-4-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)methoxycyclohexyl)-1-butene

5861-cyano-1-fluoro-4-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)oxymethylcyclohexyl)-1-butene

5871-cyano-1-fluoro-4-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)oxymethylcyclohexyl)-1-butene

5881-cyano-1-fluoro-4-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)oxymethylcyclohexyl)-1-butene

5891-cyano-1-fluoro-4-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)oxymethylcyclohexyl)-1-butene

EXAMPLE 36

Preparation of1-cyano-1-fluoro-4-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-phenylene, B¹ represents 1,4-butylene, n1 is 0,n2 is 0, n3 is 1, R² represents a group expressed by formula II, and Xrepresents fluorine atom (Compound No. 590)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that3-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)propanal was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 591 to 600) are synthesized.

5911-cyano-1-fluoro-4-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)-1-butene

5921-cyano-1-fluoro-4-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)-1-butene

5931-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

5941-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

5951-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-butylphenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

5961-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

5971-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-ethylphenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

5981-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-propylphenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

5991-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-butylphenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

6001-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-pentylphenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

EXAMPLE 37

Preparation of1-cyano-1-fluoro-4-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-cyclohexylene, B¹ represents a covalent bond,n1 is 0, n2 is 0, n3 is 0, R² represents a group expressed by formulaIII, and X represents fluorine atom (Compound No. 601)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that3-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-propenal obtainedaccording to the method of Example 13 was used as starting materialinstead of trans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 602 to 610) are synthesized.

6021-cyano-1-fluoro-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)-1,3-butadiene

6031-cyano-1-fluoro-4-(trans-4-(trans-4-butylcyclohexyl)cyclohexyl)-1,3-butadiene

6041-cyano-1-fluoro-4-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)-1,3-butadiene

6051-cyano-1-fluoro-4-(trans-4-(trans-4-heptylcyclohexyl)cyclohexyl)-1,3-butadiene

6061-cyano-1-fluoro-4-(trans-4-(2-(trans-4-ethylcyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

6071-cyano-1-fluoro-4-(trans-4-(2-(trans-4-propylcyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

6081-cyano-1-fluoro-4-(trans-4-(2-(trans-4-butylcyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

6091-cyano-1-fluoro-4-(trans-4-(2-(trans-4-pentylcyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

6101-cyano-1-fluoro-4-(trans-4-(2-(trans-4-heptylcyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

EXAMPLE 38

Preparation of1-cyano-1-fluoro-4-(trans-4-(4-ethylphenyl)cyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, n1 is0, n2 is 0, n3 is 0, R² represents a group expressed by formula III, andX represents fluorine atom (Compound No. 611)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that 3-(trans-4-(4-ethylphenyl)cyclohexyl)-2-propenalsynthesized from trans-4-(4-ethylphenyl)cyclohexanone was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 612 to 630) are synthesized.

6121-cyano-1-fluoro-4-(trans-4-(4-propylphenyl)cyclohexyl)-1,3-butadiene

613 1-cyano-1-fluoro-4-(trans-4-(4-butylphenyl)cyclohexyl)-1,3-butadiene

6141-cyano-1-fluoro-4-(trans-4-(4-pentylphenyl)cyclohexyl)-1,3-butadiene

6151-cyano-1-fluoro-4-(trans-4-(4-heptylphenyl)cyclohexyl)-1,3-butadiene

6161-cyano-1-fluoro-4-(trans-4-(2-(4-ethylphenyl)ethyl)cyclohexyl)-1,3-butadiene

6171-cyano-1-fluoro-4-(trans-4-(2-(4-propylphenyl)ethyl)cyclohexyl)-1,3-butadiene

6181-cyano-1-fluoro-4-(trans-4-(2-(4-butylphenyl)ethyl)cyclohexyl)-1,3-butadiene

6191-cyano-1-fluoro-4-(trans-4-(2-(4-pentylphenyl)ethyl)cyclohexyl)-1,3-butadiene

6201-cyano-1-fluoro-4-(trans-4-(2-(4-heptylphenyl)ethyl)cyclohexyl)-1,3-butadiene

6211-cyano-1-fluoro-4-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

6221-cyano-1-fluoro-4-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

6231-cyano-1-fluoro-4-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

6241-cyano-1-fluoro-4-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

6251-cyano-1-fluoro-4-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

6261-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-ethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

6271-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-propylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

6281-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-butylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

6291-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-pentylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

6301-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-heptylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

EXAMPLE 39

Preparation of1-cyano-1-fluoro-4-(trans-4-(2-(trans-4-ethylcyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-cyclohexylene, B¹ represents 1,2-ethenylene, n1is 0, n2 is 0, n3 is 0, R² represents a group expressed by formula III,and X represents fluorine atom (Compound No. 631)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that3-(trans-4-(2E-(trans-4-ethylcyclohexyl)ethenyl)cyclohexyl)-2-propenalsynthesized fromtrans-4-(2E-(trans-4-ethylcyclohexyl)ethenyl)cyclohexanone was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 632 to 640) are synthesized.

6321-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-propylcyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

6331-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-butylcyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

6341-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-pentylcyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

6351-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-heptylcyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

6361-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-ethylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

6371-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-propylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

6381-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-butylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

6391-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-pentylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

6401-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-heptylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

EXAMPLE 40

Preparation of trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-ethylcyclohexane carboxylate [Compound expressed by generalformula I wherein R¹ represents ethyl group, A¹ represents1,4-cyclohexylene, B¹ represents carbonyloxy, n1 is 0, n2 is 0, n3 is 0,R² represents a group expressed by formula III, and X representsfluorine atom (Compound No. 641)]

Subject compound was synthesized by the same procedures as in Example 25with the exception thattrans-4-(2-formylethenyl)cyclohexyl)trans-4-ethylcyclohexane carboxylateobtained from 4-oxocyclohexyl trans-4-ethylcyclohexane carboxylate wasused as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 642 to 671) are synthesized.

642 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-propylcyclohexane carboxylate

643 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-butylcyclohexane carboxylate

644 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-pentylcyclohexane carboxylate

645 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-hexylcyclohexane carboxylate

646 trans-4-ethylcyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

647 trans-4-propylcyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

648 trans-4-butylcyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

649 trans-4-pentylcyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

650 trans-4-hexylcyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

651 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyl 4-ethyl benzoate

652 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyl 4-propylbenzoate

653 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyl 4-butyl benzoate

654 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyl 4-pentylbenzoate

655 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyl 4-hexyl benzoate

656 4-ethylphenyl trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexanecarboxylate

657 4-propylphenyl trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexanecarboxylate

658 4-butylphenyl trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexanecarboxylate

659 4-pentylphenyl trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexanecarboxylate

660 4-hexylphenyl trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexanecarboxylate

661 4-heptylphenyl trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexanecarboxylate

662 trans-4-(4-ethylphenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

663 trans-4-(4-propylphenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

664 trans-4-(4-butylphenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

665 trans-4-(4-pentylphenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

666 trans-4-(4-hexylphenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

667 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-(4-ethylphenyl)cyclohexane carboxylate

668 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-(4-propylphenyl)cyclohexane carboxylate

669 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-(4-butylphenyl)cyclohexane carboxylate

670 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-(4-pentylphenyl)cyclohexane carboxylate

671 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-(4-hexylphenyl)cyclohexane carboxylate

EXAMPLE 41

Preparation of1-cyano-1-fluoro-4-(trans-4-(4-ethylphenyl)methoxycyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0,n2 is 0, n3 is 0, R² represents a group expressed by formula III, and Xrepresents fluorine atom (Compound No. 672)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that3-(trans-4-(4-ethylphenyl)methoxycyclohexyl)-2-propenal synthesized fromtrans-4-(4-ethylphenyl)methoxycyclohexanone was used as startingmaterial instead of trans-4-(trans-4-ethylcyclohexyl)cyclohexanecarboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 673 to 689) are synthesized.

6731-cyano-1-fluoro-4-(trans-4-(4-propylphenyl)methoxycyclohexyl)-1,3-butadiene

6741-cyano-1-fluoro-4-(trans-4-(4-butylphenyl)methoxycyclohexyl)-1,3-butadiene

6751-cyano-1-fluoro-4-(trans-4-(4-pentylphenyl)methoxycyclohexyl)-1,3-butadiene

6761-cyano-1-fluoro-4-(trans-4-(4-heptylphenyl)methoxycyclohexyl)-1,3-butadiene

6771-cyano-1-fluoro-4-(trans-4-(trans-4-propylcyclohexyl)methoxycyclohexyl)-1,3-butadiene

6781-cyano-1-fluoro-4-(trans-4-(trans-4-butylcyclohexyl)methoxycyclohexyl)-1,3-butadiene

6791-cyano-1-fluoro-4-(trans-4-(trans-4-pentylcyclohexyl)methoxycyclohexyl)-1,3-butadiene

6801-cyano-1-fluoro-4-(trans-4-(trans-4-heptylcyclohexyl)methoxycyclohexyl)-1,3-butadiene

6811-cyano-1-fluoro-4-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

6821-cyano-1-fluoro-4-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

6831-cyano-1-fluoro-4-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

6841-cyano-1-fluoro-4-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

6851-cyano-1-fluoro-4-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

6861-cyano-1-fluoro-4-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-butadiene

6871-cyano-1-fluoro-4-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-butadiene

6881-cyano-1-fluoro-4-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-butadiene

6891-cyano-1-fluoro-4-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-butadiene

EXAMPLE 42

Preparation of1-cyano-1-fluoro-4-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-phenylene, B¹ represents 1,4-butylene, n1 is 0,n2 is 0, n3 is 0, R² represents a group expressed by formula III, and Xrepresents fluorine atom (Compound No. 690)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that3-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)-2-propenal synthesizedtrans-4-(4-(4-ethylphenyl)butyl)cyclohexanone was used as startingmaterial instead of trans-4-(trans-4-ethylcyclohexyl)cyclohexanecarboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 691 to 700) are synthesized.

6911-cyano-1-fluoro-4-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)-1,3-butadiene

6921-cyano-1-fluoro-4-(trans-4-(4-(4-butylphenyl)butyl)cyclohexyl)-1,3-butadiene

6931-cyano-1-fluoro-4-(trans-4-(4-(4-heptylphenyl)butyl)cyclohexyl)-1,3-butadiene

6941-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

6951-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

6961-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-butylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

6971-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

6981-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-ethylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-butadiene

6991-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-propylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-butadiene

7001-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-butylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-butadiene

EXAMPLE 43

Preparation of1-cyano-1-fluoro-6-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-cyclohexylene, B¹ represents a covalent bond,n1 is 0, n2 is 0, n3 is 1, R² represents a group expressed by formulaIII, and X represents fluorine atom (Compound No. 701)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that5-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)-2-pentene-1-al was usedas starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 702 to 710) are synthesized.

7021-cyano-1-fluoro-6-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)-1,3-hexadiene

7031-cyano-1-fluoro-6-(trans-4-(trans-4-butylcyclohexyl)cyclohexyl)-1,3-hexadiene

7041-cyano-1-fluoro-6-(trans-4-(trans-4-pentylcyclohexyl)cyclohexyl)-1,3-hexadiene

7051-cyano-1-fluoro-6-(trans-4-(trans-4-heptylcyclohexyl)cyclohexyl)-1,3-hexadiene

7061-cyano-1-fluoro-6-(trans-4-(2-(trans-4-ethylcyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

7071-cyano-1-fluoro-6-(trans-4-(2-(trans-4-propylcyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

7081-cyano-1-fluoro-6-(trans-4-(2-(trans-4-butylcyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

7091-cyano-1-fluoro-6-(trans-4-(2-(trans-4-pentylcyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

7101-cyano-1-fluoro-6-(trans-4-(2-(trans-4-heptylcyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 44

Preparation of1-cyano-1-fluoro-6-(trans-4-(4-ethylphenyl)cyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, n1 is0, n2 is 0, n3 is 1, R² represents a group expressed by formula III, andX represents fluorine atom (Compound No. 711)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that5-(trans-4-(4-ethylphenyl)cyclohexyl)-2-pentene-1-al was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 712 to 730) are synthesized.

7121-cyano-1-fluoro-6-(trans-4-(4-propylphenyl)cyclohexyl)-1,3-hexadiene

713 1-cyano-1-fluoro-6-(trans-4-(4-butylphenyl)cyclohexyl)-1,3-hexadiene

7141-cyano-1-fluoro-6-(trans-4-(4-pentylphenyl)cyclohexyl)-1,3-hexadiene

7151-cyano-1-fluoro-6-(trans-4-(4-heptylphenyl)cyclohexyl)-1,3-hexadiene

7161-cyano-1-fluoro-6-(trans-4-(2-(4-ethylphenyl)ethyl)cyclohexyl)-1,3-hexadiene

7171-cyano-1-fluoro-6-(trans-4-(2-(4-propylphenyl)ethyl)cyclohexyl)-1,3-hexadiene

7181-cyano-1-fluoro-6-(trans-4-(2-(4-butylphenyl)ethyl)cyclohexyl)-1,3-hexadiene

7191-cyano-1-fluoro-6-(trans-4-(2-(4-pentylphenyl)ethyl)cyclohexyl)-1,3-hexadiene

7201-cyano-1-fluoro-6-(trans-4-(2-(4-heptylphenyl)ethyl)cyclohexyl)-1,3-hexadiene

7211-cyano-1-fluoro-6-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

7221-cyano-1-fluoro-6-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

7231-cyano-1-fluoro-6-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

7241-cyano-1-fluoro-6-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

7251-cyano-1-fluoro-6-(trans-4-(trans-4-(4-heptylphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

7261-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(4-ethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

7271-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(4-propylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

7281-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(4-butylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

7291-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(4-pentylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

7301-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(4-heptylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 45

Preparation of1-cyano-1-fluoro-6-(trans-4-(2-(trans-4-ethylcyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-cyclohexylene, B¹ represents 1,2-ethenylene, n1is 0, n2 is 0, n3 is 1, R² represents a group expressed by formula III,and X represents fluorine atom (Compound No. 731)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that5-(trans-4-(2E-(trans-4-ethylcyclohexyl)ethenyl)cyclohexyl)-2-pentene-1-alwas used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 732 to 740) are synthesized.

7321-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-propylcyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

7331-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-butylcyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

7341-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-pentylcyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

7351-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-heptylcyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

7361-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-(4-ethylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

7371-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-(4-propylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

7381-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-(4-butylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

7391-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-(4-pentylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

7401-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-(4-heptylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 46

Preparation of trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-ethylcyclohexane carboxylate [Compound expressed by generalformula I wherein R¹ represents ethyl group, A¹ represents1,4-cyclohexylene, B¹ represents carbonyloxy, n1 is 0, n2 is 0, n3 is 1,R² represents a group expressed by formula III, and X representsfluorine atom (Compound No. 741)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that trans-4-(4-formyl-3-butenyl)cyclohexyltrans-4-ethylcyclohexane carboxylate was used as starting materialinstead of trans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 742 to 771) are synthesized.

742 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-propylcyclohexane carboxylate

743 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-butylcyclohexane carboxylate

744 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-pentylcyclohexane carboxylate

745 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-hexylcyclohexane carboxylate

746 trans-4-ethylcyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

747 trans-4-propylcyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

748 trans-4-butylcyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

749 trans-4-pentylcyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

750 trans-4-hexylcyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

751 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyl 4-ethyl benzoate

752 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyl 4-propylbenzoate

753 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyl 4-butyl benzoate

754 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyl 4-pentylbenzoate

755 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyl 4-hexyl benzoate

756 4-ethylphenyl trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexanecarboxylate

757 4-propylphenyl trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexanecarboxylate

758 4-butylphenyl trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexanecarboxylate

759 4-pentylphenyl trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexanecarboxylate

760 4-hexylphenyl trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexanecarboxylate

761 4-heptylphenyl trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexanecarboxylate

762 trans-4-(4-ethylphenyl)cyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

763 trans-4-(4-propylphenyl)cyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

764 trans-4-(4-butylphenyl)cyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

765 trans-4-(4-pentylphenyl)cyclohexyl trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

766 trans-4-(4-hexylphenyl)cyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

767 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-(4-ethylphenyl)cyclohexane carboxylate

768 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-(4-propylphenyl)cyclohexane carboxylate

769 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-(4-butylphenyl)cyclohexane carboxylate

770 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-(4-pentylphenyl)cyclohexane carboxylate

771 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-(4-hexylphenyl)cyclohexane carboxylate

EXAMPLE 47

Preparation of1-cyano-1-fluoro-6-(trans-4-(4-ethylphenyl)methoxycyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0,n2 is 0, n3 is 1, R² represents a group expressed by formula III, and Xrepresents fluorine atom (Compound No. 772)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that5-(trans-4-(4-ethylphenyl)methoxycyclohexyl)-2-pentene-1-al was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 773 to 788) are synthesized.

7731-cyano-1-fluoro-6-(trans-4-(4-propylphenyl)methoxycyclohexyl-1,3-hexadiene

7741-cyano-1-fluoro-6-(trans-4-(4-butylphenyl)methoxycyclohexyl-1,3-hexadiene

7751-cyano-1-fluoro-6-(trans-4-(4-pentylphenyl)methoxycyclohexyl-1,3-hexadiene

7761-cyano-1-fluoro-6-(trans-4-(4-heptylphenyl)methoxycyclohexyl-1,3-hexadiene

7771-cyano-1-fluoro-6-(trans-4-(trans-4-propylcyclohexyl)methoxycyclohexyl)-1,3-hexadiene

7781-cyano-1-fluoro-6-(trans-4-(trans-4-butylcyclohexyl)methoxycyclohexyl)-1,3-hexadiene

7791-cyano-1-fluoro-6-(trans-4-(trans-4-pentylcyclohexyl)methoxycyclohexyl)-1,3-hexadiene

7801-cyano-1-fluoro-6-(trans-4-(trans-4-heptylcyclohexyl)methoxycyclohexyl)-1,3-hexadiene

7811-cyano-1-fluoro-6-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

7821-cyano-1-fluoro-6-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

7831-cyano-1-fluoro-6-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

7841-cyano-1-fluoro-6-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

7851-cyano-1-fluoro-6-(trans-4-(trans-4-(4-ethylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-hexadiene

7861-cyano-1-fluoro-6-(trans-4-(trans-4-(4-propylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-hexadiene

7871-cyano-1-fluoro-6-(trans-4-(trans-4-(4-butylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-hexadiene

7881-cyano-1-fluoro-6-(trans-4-(trans-4-(4-pentylphenyl)cyclohexyl)oxymethylcyclohexyl)-1,3-hexadiene

EXAMPLE 48

Preparation of1-cyano-1-fluoro-6-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents ethylgroup, A¹ represents 1,4-phenylene, B¹ represents 1,4-butenyl, n1 is 0,n2 is 0, n3 is 1, R² represents a group expressed by formula III, and Xrepresents fluorine atom (Compound No. 789)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that5-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)-2-pentene-1-al was usedas starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 790 to 800) are synthesized.

7901-cyano-1-fluoro-6-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)-1,3-hexadiene

7911-cyano-1-fluoro-6-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)-1,3-hexadiene

7921-cyano-1-fluoro-6-(trans-4-(4-(4-heptylphenyl)butyl)cyclohexyl)-1,3-hexadiene

7931-cyano-1-fluoro-6-(trans-4-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

7941-cyano-1-fluoro-6-(trans-4-(trans-4-(4-(4-propylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

7951-cyano-1-fluoro-6-(trans-4-(trans-4-(4-(4-pentylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

7961-cyano-1-fluoro-6-(trans-4-(trans-4-(4-(4-heptylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

7971-cyano-1-fluoro-6-(trans-4-(4-(trans-4-(4-ethylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

7981-cyano-1-fluoro-6-(trans-4-(4-(trans-4-(4-propylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

7991-cyano-1-fluoro-6-(trans-4-(4-(trans-4-(4-pentylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

800 1-cyano-1-fluoro-6-(trans-4-(4-(trans-4-(4-hexylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 49

Preparation of 1-cyano-2-(trans-4-(4-cyanophenyl)cyclohexyl)ethene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, n1 is0, n2 is 0, n3 is 0, R² represents a group expressed by formula II, andX represents hydrogen atom (Compound No. 801)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(4-cyanophenyl)cyclohexane carboaldehydewas used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

NI 169.2 to 170.0° C.

CN 147.0 to 147.9° C.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 802 to 820) are synthesized.

802 1-cyano-2-(trans-4-(4-fluorophenyl)cyclohexyl)ethene

903 1-cyano-2-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethene

804 1-cyano-2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethene

805 1-cyano-2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethene

806 1-cyano-2-(trans-4-(2-(4-cyanophenyl)ethyl)cyclohexyl)ethene

807 1-cyano-2-(trans-4-(2-(4-fluorophenyl)ethyl)cyclohexyl)ethene

808 1-cyano-2-(trans-4-(2-(3,4-difluorophenyl)ethyl)cyclohexyl)ethene

8091-cyano-2-(trans-4-(2-(4-trifluoromethylphenyl)ethyl)cyclohexyl)ethene

8101-cyano-2-(trans-4-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexyl)ethene

8111-cyano-2-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)cyclohexyl)ethene

8121-cyano-2-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)cyclohexyl)ethene

8131-cyano-2-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)cyclohexyl)ethene

8141-cyano-2-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)cyclohexyl)ethene

8151-cyano-2-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)ethene

8161-cyano-2-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)ethyl)cyclohexyl)ethene

8171-cyano-2-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)ethyl)cyclohexyl)ethene

8181-cyano-2-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethyl)cyclohexyl)ethene

8191-cyano-2-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

8201-cyano-2-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

EXAMPLE 50

Preparation of1-cyano-2-(trans-4-(2E-(trans-4-(4-cyanophenyl)cyclohexyl)ethenyl)cyclohexyl)ethene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, A²represents 1,4-cyclohexylene, B² represents 1,2-ethenylene, n1 is 0, n2is 0, n3 is 0, R² represents a group expressed by formula II, and Xrepresents hydrogen atom (Compound No. 821)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(2E-(4-cyanophenyl)ethenyl)cyclohexanecarboaldehyde was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 822 to 825) are synthesized.

8221-cyano-2-(trans-4-(2E-(trans-4-(4-fluorophenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

8231-cyano-2-(trans-4-(2E-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

8241-cyano-2-(trans-4-(2E-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

8251-cyano-2-(trans-4-(2E-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

EXAMPLE 51

Preparation of trans-4-(2-cyanoethenyl)cyclohexyl) 4-cyanobenzoate[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents carbonyloxy, n1 is 0,n2 is 0, n3 is 0, R² represents a group expressed by formula II, and Xrepresents hydrogen atom (Compound No. 826)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-formylcyclohexyl 4-cyanobenzoate wasused as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 827 to 846) are synthesized.

827 trans-4-(2-cyanoethenyl)cyclohexyl 4-fluorobenzoate

828 trans-4-(2-cyanoethenyl)cyclohexyl 3,4-difluorobenzoate

829 trans-4-(2-cyanoethenyl)cyclohexyl 4-trifluoromethyl benzoate

830 trans-4-(2-cyanoethenyl)cyclohexyl 4-trifluoromethoxybenzoate

831 4-cyanophenyl trans-4-(2-cyanoethenyl)cyclohexane carboxylate

832 4-fluorophenyl trans-4-(2-cyanoethenyl)cyclohexane carboxylate

833 3,4-difluorophenyl trans-4-(2-cyanoethenyl)cyclohexane carboxylate

834 4-trifluoromethylphenyl trans-4-(2-cyanoethenyl)cyclohexanecarboxylate

835 3-fluoro-4-cyanophenyl trans-4-(2-cyanoethenyl)cyclohexanecarboxylate

836 4-trifluoromethoxyphenyl trans-4-(2-cyanoethenyl)cyclohexanecarboxylate

837 trans-4-(4-cyanophenyl)cyclohexyltrans-4-(2-cyanoethenyl)cyclohexane carboxylate

838 trans-4-(4-fluorophenyl)cyclohexyltrans-4-(2-cyanoethenyl)cyclohexane carboxylate

839 trans-4-(3,4-difluorophenyl)cyclohexyltrans-4-(2-cyanoethenyl)cyclohexane carboxylate

840 trans-4-(4-trifluoromethylphenyl)cyclohexyltrans-4-(2-cyanoethenyl)cyclohexane carboxylate

841 trans-4-(3-fluoro-4-cyanophenyl)cyclohexyltrans-4-(2-cyanoethenyl)cyclohexane carboxylate

842 trans-4-(2-cyanoethenyl)cyclohexyltrans-4-(4-cyanophenyl)cyclohexane carboxylate

843 trans-4-(2-cyanoethenyl)cyclohexyltrans-4-(4-fluorophenyl)cyclohexane carboxylate

844 trans-4-(2-cyanoethenyl)cyclohexyltrans-4-(3,4-difluorophenyl)cyclohexane carboxylate

845 trans-4-(2-cyanoethenyl)cyclohexyltrans-4-(4-trifluoromethylphenyl)cyclohexane carboxylate

846 trans-4-(2-cyanoethenyl)cyclohexyltrans-4-(3-fluoro-4-cyanophenyl)cyclohexane carboxylate

EXAMPLE 52

Preparation of1-cyano-2-(trans-4-(4-cyanophenyl)methoxycyclohexyl)ethene [Compoundexpressed by general formula I wherein R¹ represents cyano group, A¹represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0, n2 is 0,n3 is 0, R² represents a group expressed by formula II, and X representshydrogen atom (Compound No. 847)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(4-cyanophenyl)methoxycyclohexanecarboaldehyde was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 848 to 861) are synthesized.

848 1-cyano-2-(trans-4-(4-fluorophenyl)methoxycyclohexyl)ethene

849 1-cyano-2-(trans-4-(3,4-difluorophenyl)methoxycyclohexyl)ethene

850 1-cyano-2-(trans-4-(4-trifluoromethylphenyl)methoxycyclohexyl)ethene

8511-cyano-2-(trans-4-(4-trifluoromethoxyphenyl)methoxycyclohexyl)ethene

8521-cyano-2-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)methoxycyclohexyl)ethene

8531-cyano-2-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)methoxycyclohexyl)ethene

8541-cyano-2-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)methoxycyclohexyl)ethene

8551-cyano-2-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)methoxycyclohexyl)ethene

8561-cyano-2-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)methoxycyclohexyl)ethene

8571-cyano-2-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)oxymethyl)cyclohexyl)ethene

8581-cyano-2-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)ethene

8591-cyano-2-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)ethene

8601-cyano-2-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)oxymethyl)cyclohexyl)ethene

8611-cyano-2-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)oxymethyl)cyclohexyl)ethene

EXAMPLE 53

Preparation of1-cyano-2-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)ethene [Compoundexpressed by general formula I wherein R¹ represents cyano group, A¹represents 1,4-phenylene, B¹ represents 1,4-butylene, n1 is 0, n2 is 0,n3 is 0, R² represents a group expressed by formula II, and X representshydrogen atom (Compound No. 862)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(4-(4-cyanophenyl)butyl)cyclohexanecarboaldehyde was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 863 to 876) are synthesized.

863 1-cyano-2-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)ethene

864 1-cyano-2-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)ethene

8651-cyano-2-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)ethene

8661-cyano-2-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)ethene

8671-cyano-2-(trans-4-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)cyclohexyl)ethene

8681-cyano-2-(trans-4-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)cyclohexyl)ethene

8691-cyano-2-(trans-4-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)cyclohexyl)ethene

8701-cyano-2-(trans-4-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)cyclohexyl)ethene

8711-cyano-2-(trans-4-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)cyclohexyl)ethene

8721-cyano-2-(trans-4-(4-(trans-4-(4-cyanophenyl)cyclohexyl)butyl)cyclohexyl)ethene

8731-cyano-2-(trans-4-(4-(trans-4-(4-fluorophenyl)cyclohexyl)butyl)cyclohexyl)ethene

8741-cyano-2-(trans-4-(4-(trans-4-(3,4-difluorophenyl)cyclohexyl)butyl)cyclohexyl)ethene

8751-cyano-2-(trans-4-(4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)butyl)cyclohexyl)ethene

8761-cyano-2-(trans-4-(4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)butyl)cyclohexyl)ethene

EXAMPLE 54

Preparation of 1-cyano-4-(trans-4-(4-cyanophenyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, n1 is0, n2 is 0, n3 is 1, R² represents a group expressed by formula II, andX represents hydrogen atom (Compound No. 877)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that 3-(trans-4-(4-cyanophenyl)cyclohexyl propanalwas used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 878 to 896) are synthesized.

878 1-cyano-4-(trans-4-(4-fluorophenyl)cyclohexyl)-1-butene

879 1-cyano-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)-1-butene

880 1-cyano-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)-1-butene

881 1-cyano-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)-1-butene

882 1-cyano-4-(trans-4-(2-(4-cyanophenyl)ethyl)cyclohexyl)-1-butene

883 1-cyano-4-(trans-4-(2-(4-fluorophenyl)ethyl)cyclohexyl)-1-butene

884 1-cyano-4-(trans-4-(2-(3,4-difluorophenyl)ethyl)cyclohexyl)-1-butene

8851-cyano-4-(trans-4-(2-(4-trifluoromethylphenyl)ethyl)cyclohexyl)-1-butene

8861-cyano-4-(trans-4-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexyl)-1-butene

8871-cyano-4-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)cyclohexyl)-1-butene

8881-cyano-4-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)cyclohexyl)-1-butene

8891-cyano-4-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)cyclohexyl)-1-butene

8901-cyano-4-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-1-butene

8911-cyano-4-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1-butene

8921-cyano-4-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

8931-cyano-4-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

8941-cyano-4-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

8951-cyano-4-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

8961-cyano-4-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

EXAMPLE 55

Preparation of1-cyano-4-(trans-4-(2E-(trans-4-(4-cyanophenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents covalent bond, A²represents 1,4-cyclohexylene, B² represents 1,2-ethenylene, n1 is 1, n2is 0, n3 is 1, R² represents a group expressed by formula II, and Xrepresents hydrogen atom (Compound No. 897)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that 3-(trans-4-(2E-(4-cyanophenyl)ethenyl)cyclohexylpropanal was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 898 to 901) are synthesized.

8981-cyano-4-(trans-4-(2E-(trans-4-(4-fluorophenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

8991-cyano-4-(trans-4-(2E-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

9001-cyano-4-(trans-4-(2E-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

9011-cyano-4-(trans-4-(2E-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

EXAMPLE 56

Preparation of trans-(4-cyano-3-butenyl)cyclohexyl 4-cyanobenzoate[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents carbonyloxy, n1 is 0,n2 is 0, n3 is 1, R² represents a group expressed by formula II, and Xrepresents hydrogen atom (Compound No. 902)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(2-formylethyl)cyclohexyl4-cyanobenzoate was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 903 to 922) are synthesized.

903 trans-4-(4-cyano-3-butenyl)cyclohexyl 4-fluorobenzoate

904 trans-4-(4-cyano-3-butenyl)cyclohexyl 3,4-difluorobenzoate

905 trans-4-(4-cyano-3-butenyl)cyclohexyl 4-trifluoromethylbenzoate

906 trans-4-(4-cyano-3-butenyl)cyclohexyl 4-trifluoromethoxybenzoate

907 4-cyanophenyl trans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

908 4-fluorophenyl trans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

909 3,4-difluorophenyl trans-4-(4-cyano-3-butenyl)cyclohexanecarboxylate

910 4-trifluoromethylphenyl trans-4-(4-cyano-3-butenyl)cyclohexanecarboxylate

911 3-fluoro-4-cyanophenyl trans-4-(4-cyano-3-butenyl)cyclohexanecarboxylate

912 4-trifluoromethoxyphenyl trans-4-(4-cyano-3-butenyl)cyclohexanecarboxylate

913 trans-4-(4-cyanophenyl)cyclohexyltrans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

914 trans-4-(4-fluorophenyl)cyclohexyltrans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

915 trans-4-(3,4-difluorophenyl)cyclohexyltrans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

916 trans-4-(4-trifluoromethylphenyl)cyclohexyltrans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

917 trans-4-(3-fluoro-4-cyanophenyl)cyclohexyltrans-4-(4-cyano-3-butenyl)cyclohexane carboxylate

918 trans-4-(4-cyano-3-butenyl)cyclohexyltrans-4-(4-cyanophenyl)cyclohexane carboxylate

919 trans-4-(4-cyano-3-butenyl)cyclohexyltrans-4-(4-fluorophenyl)cyclohexane carboxylate

920 trans-4-(4-cyano-3-butenyl)cyclohexyltrans-4-(3,4-difluorophenyl)cyclohexane carboxylate

921 trans-4-(4-cyano-3-butenyl)cyclohexyltrans-4-(4-trifluoromethylphenyl)cyclohexane carboxylate

922 trans-4-(4-cyano-3-butenyl)cyclohexyltrans-4-(3-fluoro-4-cyanophenyl)cyclohexane carboxylate

EXAMPLE 57

Preparation of1-cyano-4-(trans-4-(4-cyanophenyl)methoxycyclohexyl)-1-butene [Compoundexpressed by general formula I wherein R¹ represents cyano group, A¹represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0, n2 is 0,n3 is 1, R² represents a group expressed by formula II, and X representshydrogen atom (Compound No. 923)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that 3-trans-4-(4-cyanophenyl)methoxycyclohexylpropanal was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 924 to 937) are synthesized.

924 1-cyano-4-(trans-4-(4-fluorophenyl)methoxycyclohexyl)-1-butene

925 1-cyano-4-(trans-4-(3,4-difluorophenyl)methoxycyclohexyl)-1-butene

9261-cyano-4-(trans-4-(4-trifluoromethylphenyl)methoxycyclohexyl)-1-butene

9271-cyano-4-(trans-4-(4-trifluoromethoxyphenyl)methoxycyclohexyl)-1-butene

9281-cyano-4-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)methoxycyclohexyl)-1-butene

9291-cyano-4-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)methoxycyclohexyl)-1-butene

9301-cyano-4-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)methoxycyclohexyl)-1-butene

9311-cyano-4-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)methoxycyclohexyl)-1-butene

9321-cyano-4-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)methoxycyclohexyl)-1-butene

9331-cyano-4-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1-butene

9341-cyano-4-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1-butene

9351-cyano-4-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1-butene

9361-cyano-4-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)oxymethyl)cyclohexyl)-1-butene

9371-cyano-4-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)oxymethyl)cyclohexyl)-1-butene

EXAMPLE 58

Preparation of1-cyano-4-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents 1,4-butylene, n1 is 0,n2 is 0, n3 is 1, R² represents a group expressed by formula II, and Xrepresents hydrogen atom (Compound No. 938)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that 3-trans-4-(4-(4-cyanophenyl)butyl)cyclohexylpropanal was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 939 to 952) are synthesized.

939 1-cyano-4-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)-1-butene

940 1-cyano-4-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)-1-butene

9411-cyano-4-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)-1-butene

9421-cyano-4-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)-1-butene

9431-cyano-4-(trans-4-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

9441-cyano-4-(trans-4-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

9451-cyano-4-(trans-4-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

9461-cyano-4-(trans-4-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

9471-cyano-4-(trans-4-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

9481-cyano-4-(trans-4-(4-(trans-4-(4-cyanophenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

9491-cyano-4-(trans-4-(4-(trans-4-(4-fluorophenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

9501-cyano-4-(trans-4-(4-(trans-4-(3,4-difluorophenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

9511-cyano-4-(trans-4-(4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

9521-cyano-4-(trans-4-(4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

EXAMPLE 59

Preparation of1-cyano-4-(trans-4-(4-cyanophenyl)cyclohexyl)-1,3-butadiene [Compoundexpressed by general formula I wherein R¹ represents cyano group, A¹represents 1,4-phenylene, B¹ represents a covalent bond, n1 is 0, n2 is0, n3 is 0, R² represents a group expressed by formula III, and Xrepresents hydrogen atom (Compound No. 953)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that3-(trans-4-(4-cyanophenyl)cyclohexyl-2-propene-1-al was used as startingmaterial instead of trans-4-(trans-4-ethylcyclohexyl)cyclohexanecarboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 954 to 972) are synthesized.

954 1-cyano-4-(trans-4-(4-fluorophenyl)cyclohexyl)-1,3-butadiene

955 1-cyano-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)-1,3-butadiene

9561-cyano-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)-1,3-butadiene

9571-cyano-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)-1,3-butadiene

958 1-cyano-4-(trans-4-(2-(4-cyanophenyl)ethyl)cyclohexyl)-1,3-butadiene

9591-cyano-4-(trans-4-(2-(4-fluorophenyl)ethyl)cyclohexyl)-1,3-butadiene

9601-cyano-4-(trans-4-(2-(3,4-difluorophenyl)ethyl)cyclohexyl)-1,3-butadiene

9611-cyano-4-(trans-4-(2-(4-trifluoromethylphenyl)ethyl)cyclohexyl)-1,3-butadiene

9621-cyano-4-(trans-4-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexyl)-1,3-butadiene

9631-cyano-4-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

9641-cyano-4-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

9651-cyano-4-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

9661-cyano-4-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

9671-cyano-4-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

9681-cyano-4-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

9691-cyano-4-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

9701-cyano-4-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

9711-cyano-4-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

9721-cyano-4-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

EXAMPLE 60

Preparation of1-cyano-4-(trans-4-(2E-(trans-4-(4-cyanophenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, A²represents 1,4-cyclohexylene, B² represents 1,2-ethenylene, n1 is 1, n2is 0, n3 is 0, R² represents a group expressed by formula III, and Xrepresents hydrogen atom (Compound No. 973)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that3-(trans-4-(2E-(4-cyanophenyl)ethenyl)cyclohexyl-2-propene-1-al was usedas starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 973 to 976) are synthesized.

9731-cyano-4-(trans-4-(2E-(trans-4-(4-fluorophenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

9741-cyano-4-(trans-4-(2E-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

9751-cyano-4-(trans-4-(2E-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

9761-cyano-4-(trans-4-(2E-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

EXAMPLE 61

Preparation of trans-4-(4-cyano-1,3-butadienyl)cyclohexyl4-ethylbenzoate [Compound expressed by general formula I wherein R¹represents cyano group, A¹ represents 1,4-phenylene, B¹ representscarbonyloxy, n1 is 0, n2 is 0, n3 is 0, R² represents a group expressedby formula III, and X represents hydrogen atom (Compound No. 977)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(2-formylethyl)cyclohexyl 4-cyanobenzoate was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 978 to 997) are synthesized.

978 trans-4-(4-cyano-1,3-butadienyl)cyclohexyl 4-fluorobenzoate

979 trans-4-(4-cyano-1,3-butadienyl)cyclohexyl 3,4-difluorobenzoate

980 trans-4-(4-cyano-1,3-butadienyl)cyclohexyl 4-trifluoromethylbenzoate

981 trans-4-(4-cyano-1,3-butadienyl)cyclohexyl4-trifluoromethoxybenzoate

982 4-cyanophenyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

983 4-fluorophenyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

984 3,4-difluorophenyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

985 4-trifluoromethylphenyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

986 3-fluoro-4-cyanophenyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

987 4-trifluoromethoxyphenyl trans-4-(4-cyano-1,3-butadienyl)cyclohexanecarboxylate

988 trans-4-(4-cyanophenyl)cyclohexyltrans-4-(4-cyano-1,3-butadienyl)cyclohexane carboxylate

989 trans-4-(4-fluorophenyl)cyclohexyltrans-4-(4-cyano-1,3-butadienyl)cyclohexane carboxylate

990 trans-4-(3,4-difluorophenyl)cyclohexyltrans-4-(4-cyano-1,3-butadienyl)cyclohexane carboxylate

991 trans-4-(4-trifluoromethylphenyl)cyclohexyltrans-4-(4-cyano-1,3-butadienyl)cyclohexane carboxylate

992 trans-4-(3-fluoro-4-cyanophenyl)cyclohexyltrans-4-(4-cyano-1,3-butadienyl)cyclohexane carboxylate

993 trans-4-(4-cyano-1,3-butadienyl)cyclohexyltrans-4-(4-cyanophenyl)cyclohexane carboxylate

994 trans-4-(4-cyano-1,3-butadienyl)cyclohexyltrans-4-(4-fluorophenyl)cyclohexane carboxylate

995 trans-4-(4-cyano-1,3-butadienyl)cyclohexyltrans-4-(3,4-difluorophenyl)cyclohexane carboxylate

996 trans-4-(4-cyano-1,3-butadienyl)cyclohexyltrans-4-(4-trifluoromethylphenyl)cyclohexane carboxylate

997 trans-4-(4-cyano-1,3-butadienyl)cyclohexyltrans-4-(3-fluoro-4-cyanophenyl)cyclohexane carboxylate

EXAMPLE 62

Preparation of1-cyano-4-(trans-4-(4-cyanophenyl)methoxycyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0,n2 is 0, n3 is 0, R² represents a group expressed by formula III, and Xrepresents hydrogen atom (Compound No. 998)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that3-(trans-4-(4-cyanophenyl)methoxycyclohexyl)-2-propene-1-al was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 999 to 1012) are synthesized.

999 1-cyano-4-(trans-4-(4-fluorophenyl)methoxycyclohexyl)-1,3-butadiene

10001-cyano-4-(trans-4-(3,4-difluorophenyl)methoxycyclohexyl)-1,3-butadiene

10011-cyano-4-(trans-4-(4-trifluoromethylphenyl)methoxycyclohexyl)-1,3-butadiene

10021-cyano-4-(trans-4-(4-trifluoromethoxyphenyl)methoxycyclohexyl)-1,3-butadiene

10031-cyano-4-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

10041-cyano-4-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

10051-cyano-4-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

10061-cyano-4-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

10071-cyano-4-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

10081-cyano-4-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-butadiene

10091-cyano-4-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-butadiene

10101-cyano-4-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-butadiene

10111-cyano-4-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-butadiene

10121-cyano-4-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-butadiene

EXAMPLE 63

Preparation of1-cyano-4-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents 1,4-butylene, n1 is 0,n2 is 0, n3 is 0, R² represents a group expressed by formula III, and Xrepresents hydrogen atom (Compound No. 1013)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that3-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)-2-propene-1-al was usedas starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1014 to 1027) are synthesized.

10141-cyano-4-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)-1,3-butadiene

10151-cyano-4-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)-1,3-butadiene

10161-cyano-4-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)-1,3-butadiene

10171-cyano-4-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)-1,3-butadiene

10181-cyano-4-(trans-4-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

10191-cyano-4-(trans-4-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

10201-cyano-4-(trans-4-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

10211-cyano-4-(trans-4-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

10221-cyano-4-(trans-4-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

10231-cyano-4-(trans-4-(4-(trans-4-(4-cyanophenyl)cyclohexyl)butyl)cyclohexyl)-1,3-butadiene

10241-cyano-4-(trans-4-(4-(trans-4-(4-fluorophenyl)cyclohexyl)butyl)cyclohexyl)-1,3-butadiene

10251-cyano-4-(trans-4-(4-(trans-4-(3,4-difluorophenyl)cyclohexyl)butyl)cyclohexyl)-1,3-butadiene

10261-cyano-4-(trans-4-(4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-butadiene

10271-cyano-4-(trans-4-(4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-butadiene

EXAMPLE 64

Preparation of1-cyano-6-(trans-4-(4-cyanophenyl)cyclohexyl)-1,3-hexadiene [Compoundexpressed by general formula I wherein R¹ represents cyano group, A¹represents 1,4-phenylene, B¹ represents a covalent bond, n1 is 0, n2 is0, n3 is 1, R² represents a group expressed by formula III, and Xrepresents hydrogen atom (Compound No. 1028)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that5-(trans-4-(4-cyanophenyl)cyclohexyl)-2-pentene-1-al was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1029 to 1047) are synthesized.

1029 1-cyano-6-(trans-4-(4-fluorophenyl)cyclohexyl)-1,3-hexadiene

1030 1-cyano-6-(trans-4-(3,4-difluorophenyl)cyclohexyl)-1,3-hexadiene

10311-cyano-6-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)-1,3-hexadiene

10321-cyano-6-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)-1,3-hexadiene

10331-cyano-6-(trans-4-(2-(4-cyanophenyl)ethyl)cyclohexyl)-1,3-hexadiene

10341-cyano-6-(trans-4-(2-(4-fluorophenyl)ethyl)cyclohexyl)-1,3-hexadiene

10351-cyano-6-(trans-4-(2-(3,4-difluorophenyl)ethyl)cyclohexyl)-1,3-hexadiene

10361-cyano-6-(trans-4-(2-(4-trifluoromethylphenyl)ethyl)cyclohexyl)-1,3-hexadiene

10371-cyano-6-(trans-4-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexyl)-1,3-hexadiene

10381-cyano-6-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

10391-cyano-6-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

10401-cyano-6-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

10411-cyano-6-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

10421-cyano-6-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

10431-cyano-6-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

10441-cyano-6-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

10451-cyano-6-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

10461-cyano-6-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

10471-cyano-6-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 65

Preparation of1-cyano-6-(trans-4-(2E-(trans-4-(4-cyanophenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, A²represents 1,4-cyclohexylene, B² represents 1,2-ethenylene, n1 is 1, n2is 0, n3 is 1, R² represents a group expressed by formula III, and Xrepresents hydrogen atom (Compound No. 1048)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that5-(trans-4-(2E-(4-cyanophenyl)ethenyl)cyclohexyl)-2-pentene-1-al wasused as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1049 to 1052) are synthesized.

10491-cyano-6-(trans-4-(2E-(trans-4-(4-fluorophenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

10501-cyano-6-(trans-4-(2E-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

10511-cyano-6-(trans-4-(2E-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

10521-cyano-6-(trans-4-(2E-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 66

Preparation of trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl 4-ethylbenzoate [Compound expressed by general formula I wherein R¹ representscyano group, A¹ represents 1,4-phenylene, B¹ represents carbonyloxy, n1is 0, n2 is 0, n3 is 1, R² represents a group expressed by formula III,and X represents hydrogen atom (Compound No. 1053)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(4-formyl-3-butenyl)cyclohexyl4-cyanobenzoate was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1054 to 1073) are synthesized.

1054 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl 4-fluorobenzoate

1055 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl 3,4-difluorobenzoate

1056 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl 4-trifluoromethylbenzoate

1057 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyl4-trifluoromethoxybenzoate

1058 4-cyanophenyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

1059 4-fluorophenyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

1060 3,4-difluorophenyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

1061 4-trifluoromethylphenyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

1062 3-fluoro-4-cyanophenyl trans-4-(6-cyano-3,5-hexadienyl)cyclohexanecarboxylate

1063 4-trifluoromethoxyphenyltrans-4-(6-cyano-3,5-hexadienyl)cyclohexane carboxylate

1064 trans-4-(4-cyanophenyl)cyclohexyltrans-4-(6-cyano-3,5-hexadienyl)cyclohexane carboxylate

1065 trans-4-(4-fluorophenyl)cyclohexyltrans-4-(6-cyano-3,5-hexadienyl)cyclohexane carboxylate

1066 trans-4-(3,4-difluorophenyl)cyclohexyltrans-4-(6-cyano-3,5-hexadienyl)cyclohexane carboxylate

1067 trans-4-(4-trifluoromethylphenyl)cyclohexyltrans-4-(6-cyano-3,5-hexadienyl)cyclohexane carboxylate

1068 trans-4-(3-fluoro-4-cyanophenyl)cyclohexyltrans-4-(6-cyano-3,5-hexadienyl)cyclohexane carboxylate

1069 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyltrans-4-(4-cyanophenyl)cyclohexane carboxylate

1070 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyltrans-4-(4-fluorophenyl)cyclohexane carboxylate

1071 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyltrans-4-(3,4-difluorophenyl)cyclohexane carboxylate

1072 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyltrans-4-(4-trifluoromethylphenyl)cyclohexane carboxylate

1073 trans-4-(6-cyano-3,5-hexadienyl)cyclohexyltrans-4-(3-fluoro-4-cyanophenyl)cyclohexane carboxylate

EXAMPLE 67

Preparation of1-cyano-6-(trans-4-(4-cyanophenyl)methoxycyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0,n2 is 0, n3 is 1, R² represents a group expressed by formula III, and Xrepresents hydrogen atom (Compound No. 1074)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that5-(trans-4-(4-cyanophenyl)methoxycyclohexyl)-2-pentene-1-al was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1075 to 1088) are synthesized.

1075 1-cyano-6-(trans-4-(4-fluorophenyl)methoxycyclohexyl)-1,3-hexadiene

10761-cyano-6-(trans-4-(3,4-difluorophenyl)methoxycyclohexyl)-1,3-hexadiene

10771-cyano-6-(trans-4-(4-trifluoromethylphenyl)methoxycyclohexyl)-1,3-hexadiene

10781-cyano-6-(trans-4-(4-trifluoromethoxyphenyl)methoxycyclohexyl)-1,3-hexadiene

10791-cyano-6-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

10801-cyano-6-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

10811-cyano-6-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

10821-cyano-6-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

10831-cyano-6-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

10841-cyano-6-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-hexadiene

10851-cyano-6-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-hexadiene

10861-cyano-6-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-hexadiene

10871-cyano-6-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-hexadiene

10881-cyano-6-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 68

Preparation of1-cyano-6-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents 1,4-butylene, n1 is 0,n2 is 0, n3 is 1, R² represents a group expressed by formula III, and Xrepresents hydrogen atom (Compound No. 1089)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that5-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)-2-pentene-1-al was usedas starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1090 to 1103) are synthesized.

10901-cyano-6-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)-1,3-hexadiene

10911-cyano-6-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)-1,3-hexadiene

10921-cyano-6-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)-1,3-hexadiene

10931-cyano-6-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)-1,3-hexadiene

10941-cyano-6-(trans-4-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

10951-cyano-6-(trans-4-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

10961-cyano-6-(trans-4-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

10971-cyano-6-(trans-4-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

10981-cyano-6-(trans-4-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

10991-cyano-6-(trans-4-(4-(trans-4-(4-cyanophenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

11001-cyano-6-(trans-4-(4-(trans-4-(4-fluorophenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

11011-cyano-6-(trans-4-(4-(trans-4-(3,4-difluorophenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

11021-cyano-6-(trans-4-(4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

11031-cyano-6-(trans-4-(4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 69

Preparation of1-cyano-1-fluoro-2-(trans-4-(4-cyanophenyl)cyclohexyl)ethene [Compoundexpressed by general formula I wherein R¹ represents cyano group, A¹represents 1,4-phenylene, B¹ represents a covalent bond, n1 is 0, n2 is0, n3 is 0, R² represents a group expressed by formula II, and Xrepresents fluorine atom (Compound No. 1104)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that trans-4-(4-cyanophenyl)cyclohexane carboaldehydewas used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1105 to 1123) are synthesized.

1105 1-cyano-1-fluoro-2-(trans-4-(4-fluorophenyl)cyclohexyl)ethene

1106 1-cyano-1-fluoro-2-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethene

11071-cyano-1-fluoro-2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethene

11081-cyano-1-fluoro-2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethene

11091-cyano-1-fluoro-2-(trans-4-(2-(4-cyanophenyl)ethyl)cyclohexyl)ethene

11101-cyano-1-fluoro-2-(trans-4-(2-(4-fluorophenyl)ethyl)cyclohexyl)ethene

11111-cyano-1-fluoro-2-(trans-4-(2-(3,4-difluorophenyl)ethyl)cyclohexyl)ethene

11121-cyano-1-fluoro-2-(trans-4-(2-(4-trifluoromethylphenyl)ethyl)cyclohexyl)ethene

11131-cyano-1-fluoro-2-(trans-4-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexyl)ethene

11141-cyano-1-fluoro-2-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)cyclohexyl)ethene

11151-cyano-1-fluoro-2-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)cyclohexyl)ethene

11161-cyano-1-fluoro-2-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)cyclohexyl)ethene

11171-cyano-1-fluoro-2-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)cyclohexyl)ethene

11181-cyano-1-fluoro-2-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)ethene

11191-cyano-1-fluoro-2-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)ethyl)cyclohexyl)ethene

11201-cyano-1-fluoro-2-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)ethyl)cyclohexyl)ethene

11211-cyano-1-fluoro-2-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethyl)cyclohexyl)ethene

11221-cyano-1-fluoro-2-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

11231-cyano-1-fluoro-2-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)ethene

EXAMPLE 70

Preparation of1-cyano-1-fluoro-2-(trans-4-(2E-(trans-4-(4-cyanophenyl)cyclohexyl)ethenyl)cyclohexyl)ethene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, A²represents 1,4-cyclohexylene, B² represents 1,2-ethenylene, n1 is 1, n2is 0, n3 is 0, R² represents a group expressed by formula II, and Xrepresents fluorine atom (Compound No. 1124)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that trans-4-(2E-(4-cyanophenyl)ethenyl)cyclohexanecarboaldehyde was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1125 to 1128) are synthesized.

11251-cyano-1-fluoro-2-(trans-4-(2E-(trans-4-(4-fluorophenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

11261-cyano-1-fluoro-2-(trans-4-(2E-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

11271-cyano-1-fluoro-2-(trans-4-(2E-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

11281-cyano-1-fluoro-2-(trans-4-(2E-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethenyl)cyclohexyl)ethene

EXAMPLE 71

Preparation of trans-4-(2-cyano-2-fluoroethenyl)cyclohexyl4-ethylbenzoate [Compound expressed by general formula I wherein R¹represents cyano group, A¹ represents 1,4-phenylene, B¹ representscarbonyloxy, n1 is 0, n2 is 0, n3 is 0, R² represents a group expressedby formula II, and X represents fluorine atom (Compound No. 1129)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that trans-4-formylcyclohexyl 4-cyanobenzoate wasused as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1130 to 1149) are synthesized.

1130 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyl 4-fluorobenzoate

1131 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyl 3,4-difluorobenzoate

1132 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyl4-trifluoromethylbenzoate

1133 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyl4-trifluoromethoxybenzoate

1134 4-cyanophenyl trans-4-(2-cyano-2-fluoroethenyl)cyclohexanecarboxylate

1135 4-fluorophenyl trans-4-(2-cyano-2-fluoroethenyl)cyclohexanecarboxylate 1136 3,4-difluorophenyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

1137 4-trifluoromethylphenyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

1138 3-fluoro-4-cyanophenyl trans-4-(2-cyano-2-fluoroethenyl)cyclohexanecarboxylate

1139 4-trifluoromethoxyphenyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

1140 trans-4-(4-cyanophenyl)cyclohexyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

1141 trans-4-(4-fluorophenyl)cyclohexyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

1142 trans-4-(3,4-difluorophenyl)cyclohexyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

1143 trans-4-(4-trifluoromethylphenyl)cyclohexyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

1144 trans-4-(3-fluoro-4-cyanophenyl)cyclohexyltrans-4-(2-cyano-2-fluoroethenyl)cyclohexane carboxylate

1145 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyltrans-4-(4-cyanophenyl)cyclohexane carboxylate

1146 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyltrans-4-(4-fluorophenyl)cyclohexane carboxylate

1147 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyltrans-4-(3,4-difluorophenyl)cyclohexane carboxylate

1148 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyltrans-4-(4-trifluoromethylphenyl)cyclohexane carboxylate

1149 trans-4-(2-cyano-2-fluoroethenyl)cyclohexyltrans-4-(3-fluoro-4-cyanophenyl)cyclohexane carboxylate

EXAMPLE 72

Preparation of1-cyano-1-fluoro-2-(trans-4-(4-cyanophenyl)methoxycyclohexyl)ethene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0,n2 is 0, n3 is 0, R² represents a group expressed by formula II, and Xrepresents fluorine atom (Compound No. 1150)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that trans-4-(4-cyanophenyl)methoxycyclohexanecarboxylate was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1151 to 1164) are synthesized.

11511-cyano-1-fluoro-2-(trans-4-(4-fluorophenyl)methoxycyclohexyl)ethene

11521-cyano-1-fluoro-2-(trans-4-(3,4-difluorophenyl)methoxycyclohexyl)ethene

11531-cyano-1-fluoro-2-(trans-4-(4-trifluoromethylphenyl)methoxycyclohexyl)ethene

11541-cyano-1-fluoro-2-(trans-4-(4-trifluoromethoxyphenyl)methoxycyclohexyl)ethene

11551-cyano-1-fluoro-2-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)methoxycyclohexyl)ethene

11561-cyano-1-fluoro-2-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)methoxycyclohexyl)ethene

11571-cyano-1-fluoro-2-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)methoxycyclohexyl)ethene

11581-cyano-1-fluoro-2-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)methoxycyclohexyl)ethene

11591-cyano-1-fluoro-2-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)methoxycyclohexyl)ethene

11601-cyano-1-fluoro-2-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)oxymethyl)cyclohexyl)ethene

11611-cyano-1-fluoro-2-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)ethene

11621-cyano-1-fluoro-2-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)ethene

11631-cyano-1-fluoro-2-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)oxymethyl)cyclohexyl)ethene

11641-cyano-1-fluoro-2-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)oxymethyl)cyclohexyl)ethene

EXAMPLE 73

Preparation of1-cyano-1-fluoro-2-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)ethene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents 1,4-butylene, n1 is 0,n2 is 0, n3 is 0, R² represents a group expressed by formula II, and Xrepresents fluorine atom (Compound No. 1165)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that trans-4-(4-(4-cyanophenyl)butyl)cyclohexanecarboaldehyde was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1166 to 1179) are synthesized.

11661-cyano-1-fluoro-2-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)ethene

11671-cyano-1-fluoro-2-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)ethene

11681-cyano-1-fluoro-2-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)ethene

11691-cyano-1-fluoro-2-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)ethene

11701-cyano-1-fluoro-2-(trans-4-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)cyclohexyl)ethene

11711-cyano-1-fluoro-2-(trans-4-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)cyclohexyl)ethene

11721-cyano-1-fluoro-2-(trans-4-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)cyclohexyl)ethene

11731-cyano-1-fluoro-2-(trans-4-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)cyclohexyl)ethene

11741-cyano-1-fluoro-2-(trans-4-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)cyclohexyl)ethene

11751-cyano-1-fluoro-2-(trans-4-(4-(trans-4-(4-cyanophenyl)cyclohexyl)butyl)cyclohexyl)ethene

11761-cyano-1-fluoro-2-(trans-4-(4-(trans-4-(4-fluorophenyl)cyclohexyl)butyl)cyclohexyl)ethene

11771-cyano-1-fluoro-2-(trans-4-(4-(trans-4-(3,4-difluorophenyl)cyclohexyl)butyl)cyclohexyl)ethene

11781-cyano-1-fluoro-2-(trans-4-(4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)butyl)cyclohexyl)ethene

11791-cyano-1-fluoro-2-(trans-4-(4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)butyl)cyclohexyl)ethene

EXAMPLE 74

Preparation of1-cyano-1-fluoro-4-(trans-4-(4-cyanophenyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, n1 is0, n2 is 0, n3 is 1, R² represents a group expressed by formula II, andX represents fluorine atom (Compound No. 1180)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that 3-(trans-4-(4-cyanophenyl)cyclohexyl)propanalwas used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1181 to 1199) are synthesized.

1181 1-cyano-1-fluoro-4-(trans-4-(4-fluorophenyl)cyclohexyl)-1-butene

11821-cyano-1-fluoro-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)-1-butene

11831-cyano-1-fluoro-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)-1-butene

11841-cyano-1-fluoro-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)-1-butene

11851-cyano-1-fluoro-4-(trans-4-(2-(4-cyanophenyl)ethyl)cyclohexyl)-1-butene

11861-cyano-1-fluoro-4-(trans-4-(2-(4-fluorophenyl)ethyl)cyclohexyl)-1-butene

11871-cyano-1-fluoro-4-(trans-4-(2-(3,4-difluorophenyl)ethyl)cyclohexyl)-1-butene

11881-cyano-1-fluoro-4-(trans-4-(2-(4-trifluoromethylphenyl)ethyl)cyclohexyl)-1-butene

11891-cyano-1-fluoro-4-(trans-4-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexyl)-1-butene

11901-cyano-1-fluoro-4-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)cyclohexyl)-1-butene

11911-cyano-1-fluoro-4-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)cyclohexyl)-1-butene

11921-cyano-1-fluoro-4-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)cyclohexyl)-1-butene

11931-cyano-1-fluoro-4-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-1-butene

11941-cyano-1-fluoro-4-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1-butene

11951-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

11961-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

11971-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

11981-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

11991-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

EXAMPLE 75

Preparation of1-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-cyanophenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, A²represents 1,4-cyclohexylene, B² represents 2-ethenylene, n1 is 1, n2 is0, n3 is 1, R² represents a group expressed by formula II, and Xrepresents fluorine atom (Compound No. 1200)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that3-(trans-4-(2E-(4-cyanophenyl)ethenyl)cyclohexyl)propanal was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1201 to 1204) are synthesized.

12011-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-fluorophenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

12021-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

12031-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

12041-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethenyl)cyclohexyl)-1-butene

EXAMPLE 76

Preparation of trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyl4-ethylbenzoate [Compound expressed by general formula I wherein R¹represents cyano group, A¹ represents 1,4-phenylene, B¹ representscarbonyloxy, n1 is 0, n2 is 0, n3 is 1, R² represents a group expressedby formula II, and X represents fluorine atom (Compound No. 1205)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that trans-4-(2-formylethyl)cyclohexyl4-cyanobenzoate was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1206 to 1225) are synthesized.

1206 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyl 4-fluorobenzoate

1207 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyl 3,4-difluorobenzoate

1208 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyl4-trifluoromethylbenzoate

1209 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyl4-trifluoromethoxybenzoate

1210 4-cyanophenyl trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexanecarboxylate

1211 4-fluorophenyl trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexanecarboxylate

1212 3,4-difluorophenyl trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexanecarboxylate

1213 4-trifluoromethylphenyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

1214 3-fluoro-4-cyanophenyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

1215 4-trifluoromethoxyphenyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

1216 trans-4-(4-cyanophenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

1217 trans-4-(4-fluorophenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

1218 trans-4-(3,4-difluorophenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

1219 trans-4-(4-trifluoromethylphenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

1220 trans-4-(3-fluoro-4-cyanophenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexane carboxylate

1221 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-(4-cyanophenyl)cyclohexane carboxylate

1222 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-(4-fluorophenyl)cyclohexane carboxylate

1223 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-(3,4-difluorophenyl)cyclohexane carboxylate

1224 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-(4-trifluoromethylphenyl)cyclohexane carboxylate

1225 trans-4-(4-cyano-4-fluoro-3-butenyl)cyclohexyltrans-4-(3-fluoro-4-cyanophenyl)cyclohexane carboxylate

EXAMPLE 77

Preparation of1-cyano-1-fluoro-4-(trans-4-(4-cyanophenyl)methoxycyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0,n2 is 0, n3 is 1, R² represents a group expressed by formula II, and Xrepresents fluorine atom (Compound No. 1226)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that3-(trans-4-(4-cyanophenyl)methoxycyclohexyl)propanal was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1227 to 1240) are synthesized.

12271-cyano-1-fluoro-4-(trans-4-(4-fluorophenyl)methoxycyclohexyl)-1-butene

12281-cyano-1-fluoro-4-(trans-4-(3,4-difluorophenyl)methoxycyclohexyl)-1-butene

12291-cyano-1-fluoro-4-(trans-4-(4-trifluoromethylphenyl)methoxycyclohexyl)-1-butene

12301-cyano-1-fluoro-4-(trans-4-(4-trifluoromethoxyphenyl)methoxycyclohexyl)-1-butene

12311-cyano-1-fluoro-4-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)methoxycyclohexyl)-1-butene

12321-cyano-1-fluoro-4-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)methoxycyclohexyl)-1-butene

12331-cyano-1-fluoro-4-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)methoxycyclohexyl)-1-butene

12341-cyano-1-fluoro-4-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)methoxycyclohexyl)-1-butene

12351-cyano-1-fluoro-4-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)methoxycyclohexyl)-1-butene

12361-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1-butene

12371-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1-butene

12381-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1-butene

12391-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)oxymethyl)cyclohexyl)-1-butene

12401-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)oxymethyl)cyclohexyl)-1-butene

EXAMPLE 78

Preparation of1-cyano-1-fluoro-4-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)-1-butene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents 1,4-butylene, n1 is 0,n2 is 0, n3 is 1, R² represents a group expressed by formula II, and Xrepresents fluorine atom (Compound No. 1241)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that3-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)propanal was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1242 to 1255) are synthesized.

12421-cyano-1-fluoro-4-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)-1-butene

12431-cyano-1-fluoro-4-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)-1-butene

12441-cyano-1-fluoro-4-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)-1-butene

12451-cyano-1-fluoro-4-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)-1-butene

12461-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

12471-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

12481-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

12491-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

12501-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)cyclohexyl)-1-butene

12511-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-cyanophenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

12521-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-fluorophenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

12531-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(3,4-difluorophenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

12541-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

12551-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)butyl)cyclohexyl)-1-butene

EXAMPLE 79

Preparation of1-cyano-1-fluoro-4-(trans-4-(4-cyanophenyl)cyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, n1 is0, n2 is 0, n3 is 0, R² represents a group expressed by formula III, andX represents fluorine atom (Compound No. 1256)]

Subject compound was synthesized by the same procedures as in Example 25with the exception that 3-(trans-4-(4-cyanophenyl)cyclohexyl)-2-propenalwas used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1257 to 1275) are synthesized.

12571-cyano-1-fluoro-4-(trans-4-(4-fluorophenyl)cyclohexyl)-1,3-butadiene

12581-cyano-1-fluoro-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)-1,3-butadiene

12591-cyano-1-fluoro-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)-1,3-butadiene

12601-cyano-1-fluoro-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)-1,3-butadiene

12611-cyano-1-fluoro-4-(trans-4-(2-(4-cyanophenyl)ethyl)cyclohexyl)-1,3-butadiene

12621-cyano-1-fluoro-4-(trans-4-(2-(4-fluorophenyl)ethyl)cyclohexyl)-1,3-butadiene

12631-cyano-1-fluoro-4-(trans-4-(2-(3,4-difluorophenyl)ethyl)cyclohexyl)-1,3-butadiene

12641-cyano-1-fluoro-4-(trans-4-(2-(4-trifluoromethylphenyl)ethyl)cyclohexyl)-1,3-butadiene

12651-cyano-1-fluoro-4-(trans-4-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexyl)-1,3-butadiene

12661-cyano-1-fluoro-4-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

12671-cyano-1-fluoro-4-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

12681-cyano-1-fluoro-4-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

12691-cyano-1-fluoro-4-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

12701-cyano-1-fluoro-4-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1,3-butadiene

12711-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

12721-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

12731-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

12741-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

12751-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-butadiene

EXAMPLE 80

Preparation of1-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-cyanophenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, A²represents 1,4-cyclohexylene, B² represents 1,2-ethenylene, ni is 1, n2is 0, n3 is 0, R² represents a group expressed by formula III, and Xrepresents fluorine atom (Compound No. 1256)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that3-(trans-4-(2E-(4-cyanophenyl)ethenyl)cyclohexyl)propenal was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1277 to 1280) are synthesized.

12771-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-fluorophenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

12781-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

12791-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

12801-cyano-1-fluoro-4-(trans-4-(2E-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-butadiene

EXAMPLE 81

Preparation of trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyl4-cyanobenzoate [Compound expressed by general formula I wherein R¹represents cyano group, A¹ represents 1,4-phenylene, B¹ representscarbonyloxy, n1 is 0, n2 is 0, n3 is 0, R² represents a group expressedby formula III, and X represents fluorine atom (Compound No. 1281)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(2-formylethenyl)cyclohexyl4-cyanobenzoate was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1282 to 1301) are synthesized.

1282 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyl4-fluorobenzoate

1283 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyl3,4-difluorobenzoate

1284 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyl4-trifluoromethylbenzoate

1285 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyl4-trifluoromethoxybenzoate

1286 4-cyanophenyl trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexanecarboxylate

1287 4-fluorophenyl trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexanecarboxylate

1288 3,4-difluorophenyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

1289 4-trifluoromethylphenyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

1290 3-fluoro-4-cyanophenyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

1291 4-trifluoromethoxyphenyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

1292 trans-4-(4-cyanophenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

1293 trans-4-(4-fluorophenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

1294 trans-4-(3,4-difluorophenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

1295 trans-4-(4-trifluoromethylphenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

1296 trans-4-(3-fluoro-4-cyanophenyl)cyclohexyltrans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexane carboxylate

1297 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-(4-cyanophenyl)cyclohexane carboxylate

1298 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-(4-fluorophenyl)cyclohexane carboxylate

1299 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-(3,4-difluorophenyl)cyclohexane carboxylate

1300 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-(4-trifluoromethylphenyl)cyclohexane carboxylate

1301 trans-4-(4-cyano-4-fluoro-1,3-butadienyl)cyclohexyltrans-4-(3-fluoro-4-cyanophenyl)cyclohexane carboxylate

EXAMPLE 82

Preparation of1-cyano-1-fluoro-4-(trans-4-(4-cyanophenyl)methoxycyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0,n2 is 0, n3 is 0, R² represents a group expressed by formula III, and Xrepresents fluorine atom (Compound No. 1302)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that3-(trans-4-(4-cyanophenyl)methoxycyclohexyl)-2-propene-1-al was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1303 to 1316) are synthesized.

13031-cyano-1-fluoro-4-(trans-4-(4-fluorophenyl)methoxycyclohexyl)-1,3-butadiene

13041-cyano-1-fluoro-4-(trans-4-(3,4-difluorophenyl)methoxycyclohexyl)-1,3-butadiene

13051-cyano-1-fluoro-4-(trans-4-(4-trifluoromethylphenyl)methoxycyclohexyl)-1,3-butadiene

13061-cyano-1-fluoro-4-(trans-4-(4-trifluoromethoxyphenyl)methoxycyclohexyl)-1,3-butadiene

13071-cyano-1-fluoro-4-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

13081-cyano-1-fluoro-4-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

13091-cyano-1-fluoro-4-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

13101-cyano-1-fluoro-4-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

13111-cyano-1-fluoro-4-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)methoxycyclohexyl)-1,3-butadiene

13121-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-butadiene

13131-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-butadiene

13141-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-butadiene

13151-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-butadiene

13161-cyano-1-fluoro-4-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-butadiene

EXAMPLE 83

Preparation of1-cyano-1-fluoro-4-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)-1,3-butadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents 1,4-butylene, n1 is 0,n2 is 0, n3 is 0, R² represents a group expressed by formula III, and Xrepresents fluorine atom (Compound No. 1317)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that3-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)-2-propene-1-al was usedas starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1318 to 1331) are synthesized.

13181-cyano-1-fluoro-4-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)-1,3-butadiene

13191-cyano-1-fluoro-4-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)-1,3-butadiene

13201-cyano-1-fluoro-4-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)-1,3-butadiene

13211-cyano-1-fluoro-4-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)-1,3-butadiene

13221-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

13231-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

13241-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

13251-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

13261-cyano-1-fluoro-4-(trans-4-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-butadiene

13271-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-cyanophenyl)cyclohexyl)butyl)cyclohexyl-1,3-butadiene

13281-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-fluorophenyl)cyclohexyl)butyl)cyclohexyl-1,3-butadiene

13291-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(3,4-difluorophenyl)cyclohexyl)butyl)cyclohexyl-1,3-butadiene

13301-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)butyl)cyclohexyl-1,3-butadiene

13311-cyano-1-fluoro-4-(trans-4-(4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)butyl)cyclohexyl-1,3-butadiene

EXAMPLE 84

Preparation of1-cyano-1-fluoro-6-(trans-4-(4-cyanophenyl)cyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, n1 is0, n2 is 0, n3 is 1, R² represents a group expressed by formula III, andX represents fluorine atom (Compound No. 1332)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that5-(trans-4-(4-cyanophenyl)cyclohexyl)-2-pentene-1-al was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1333 to 1351) are synthesized.

13331-cyano-1-fluoro-6-(trans-4-(4-fluorophenyl)cyclohexyl)-1,3-hexadiene

13341-cyano-1-fluoro-6-(trans-4-(3,4-difluorophenyl)cyclohexyl)-1,3-hexadiene

13351-cyano-1-fluoro-6-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)-1,3-hexadiene

13361-cyano-1-fluoro-6-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)-1,3-hexadiene

13371-cyano-1-fluoro-6-(trans-4-(2-(4-cyanophenyl)ethyl)cyclohexyl)-1,3-hexadiene

13381-cyano-1-fluoro-6-(trans-4-(2-(4-fluorophenyl)ethyl)cyclohexyl)-1,3-hexadiene

13391-cyano-1-fluoro-6-(trans-4-(2-(3,4-difluorophenyl)ethyl)cyclohexyl)-1,3-hexadiene

13401-cyano-1-fluoro-6-(trans-4-(2-(4-trifluoromethylphenyl)ethyl)cyclohexyl)-1,3-hexadiene

13411-cyano-1-fluoro-6-(trans-4-(2-(4-trifluoromethoxyphenyl)ethyl)cyclohexyl)-1,3-hexadiene

13421-cyano-1-fluoro-6-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

13431-cyano-1-fluoro-6-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

13441-cyano-1-fluoro-6-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

13451-cyano-1-fluoro-6-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

13461-cyano-1-fluoro-6-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

13471-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

13481-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

13491-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

13501-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

13511-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 85

Preparation of1-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-(4-cyanophenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents a covalent bond, A²represents 1,4-cyclohexylene, B² represents 1,2-ethenylene, n1 is 1, n2is 0, n3 is 1, R² represents a group expressed by formula III, and Xrepresents fluorine atom (Compound No. 1352)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that5-(trans-4-(2E-(4-cyanophenyl)ethenyl)cyclohexyl)-2-pentene-1-al wasused as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1353 to 1356) are synthesized.

13531-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-(4-fluorophenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

13541-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-(3,4-difluorophenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

13551-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

13561-cyano-1-fluoro-6-(trans-4-(2E-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)ethenyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 86

Preparation of trans-4-(2-cyano-2-fluoro-3,5-hexadienyl)cyclohexyl4-ethyl benzoate [Compound expressed by general formula I wherein R¹represents cyano group, A¹ represents 1,4-phenylene, B¹ representscarbonyloxy, n1 is 0, n2 is 0, n3 is 1, R² represents a group expressedby formula III, and X represents fluorine atom (Compound No. 1357)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that trans-4-(4-formyl-3-butene-1-yl)cyclohexyl4-cyanobenzoate was used as starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1358 to 1377) are synthesized.

1358 trans-4-(6-cyano-6-fluoro-3,5-hexadieneyl)cyclohexyl4-fluorobenzoate

1359 trans-4-(6-cyano-6-fluoro-3,5-hexadieneyl)cyclohexyl3,4-difluorobenzoate

1360 trans-4-(6-cyano-6-fluoro-3,5-hexadieneyl)cyclohexyl4-trifluoromethyl benzoate

1361 trans-4-(6-cyano-6-fluoro-3,5-hexadieneyl)cyclohexyl4-trifluoromethoxy benzoate

1362 4-cyanophenyl trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexanecarboxylate

1363 4-fluorophenyl trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexanecarboxylate

1364 3,4-difluorophenyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

1365 4-trifluoromethylphenyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

1366 3-fluoro-4-cyanophenyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

1367 4-trifluoromethoxyphenyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

1368 trans-4-(4-cyanophenyl)cyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

1369 trans-4-(4-fluorophenyl)cyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

1370 trans-4-(3,4-difluorophenyl)cyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

1371 trans-4-(4-trifluoromethylphenyl)cyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

1372 trans-4-(3-fluoro-4-cyanophenyl)cyclohexyltrans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexane carboxylate

1373 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-(4-cyanophenyl)cyclohexane carboxylate

1374 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-(4-fluorophenyl)cyclohexane carboxylate

1375 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-(3,4-difluorophenyl)cyclohexane carboxylate

1376 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-(4-trifluoromethylphenyl)cyclohexane carboxylate

1377 trans-4-(6-cyano-6-fluoro-3,5-hexadienyl)cyclohexyltrans-4-(3-fluoro-4-cyanophenyl)cyclohexane carboxylate

EXAMPLE 87

Preparation of1-cyano-1-fluoro-6-(trans-4-(4-cyanophenyl)methoxycyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents methyleneoxy, n1 is 0,n3 is 1, R² represents a group expressed by formula III, and Xrepresents fluorine atom (Compound No. 1378)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that5-(trans-4-(4-cyanophenyl)methoxycyclohexyl)-2-pentene-1-al was used asstarting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1379 to 1392) are synthesized.

13791-cyano-1-fluoro-6-(trans-4-(4-fluorophenyl)methoxycyclohexyl)-1,3-hexadiene

13801-cyano-1-fluoro-6-(trans-4-(3,4-difluorophenyl)methoxycyclohexyl)-1,3-hexadiene

13811-cyano-1-fluoro-6-(trans-4-(4-trifluoromethylphenyl)methoxycyclohexyl)-1,3-hexadiene

13821-cyano-1-fluoro-6-(trans-4-(4-trifluoromethoxyphenyl)methoxycyclohexyl)-1,3-hexadiene

13831-cyano-1-fluoro-6-(trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

13841-cyano-1-fluoro-6-(trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

13851-cyano-1-fluoro-6-(trans-4-(trans-4-(3,4-difluorophenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

13861-cyano-1-fluoro-6-(trans-4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

13871-cyano-1-fluoro-6-(trans-4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)methoxycyclohexyl)-1,3-hexadiene

13881-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(4-cyanophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-hexadiene

13891-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(4-fluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-hexadiene

13901-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(3,4-difluorophenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-hexadiene

13911-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-hexadiene

13921-cyano-1-fluoro-6-(trans-4-(2-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)oxymethyl)cyclohexyl)-1,3-hexadiene

EXAMPLE 88

Preparation of1-cyano-1-fluoro-6-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)-1,3-hexadiene[Compound expressed by general formula I wherein R¹ represents cyanogroup, A¹ represents 1,4-phenylene, B¹ represents 1,4-butylene, n1 is 0,n2 is 0, n3 is 1, R² represents a group expressed by formula III, and Xrepresents fluorine atom (Compound No. 1393)]

Subject compound was synthesized by the same procedures as in Example 1with the exception that5-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)-2-pentene-1-al was usedas starting material instead oftrans-4-(trans-4-ethylcyclohexyl)cyclohexane carboaldehyde.

By the procedures similar to those described above, the followingcompounds (Compound Nos. 1394 to 1407) are synthesized.

13941-cyano-1-fluoro-6-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)-1,3-hexadiene

13951-cyano-1-fluoro-6-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)-1,3-hexadiene

13961-cyano-1-fluoro-6-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)-1,3-hexadiene

13971-cyano-1-fluoro-6-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)-1,3-hexadiene

13981-cyano-1-fluoro-6-(trans-4-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

13991-cyano-1-fluoro-6-(trans-4-(trans-4-(4-(4-fluorophenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

14001-cyano-1-fluoro-6-(trans-4-(trans-4-(4-(3,4-difluorophenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

14011-cyano-1-fluoro-6-(trans-4-(trans-4-(4-(4-trifluoromethylphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

14021-cyano-1-fluoro-6-(trans-4-(trans-4-(4-(4-trifluoromethoxyphenyl)butyl)cyclohexyl)cyclohexyl)-1,3-hexadiene

14031-cyano-1-fluoro-6-(trans-4-(4-(trans-4-(4-cyanophenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

14041-cyano-1-fluoro-6-(trans-4-(4-(trans-4-(4-fluorophenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

14051-cyano-1-fluoro-6-(trans-4-(4-(trans-4-(3,4-difluorophenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

14061-cyano-1-fluoro-6-(trans-4-(4-(trans-4-(4-trifluoromethylphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

14071-cyano-1-fluoro-6-(trans-4-(4-(trans-4-(4-trifluoromethoxyphenyl)cyclohexyl)butyl)cyclohexyl)-1,3-hexadiene

Now, examples of compositions in which the compounds of the presentinvention are used are described.

In the examples, compounds are indicated according to the definitionshown in Table 1 in the same way as those described above. Further, "%"indicating the content of each compound means "% by weight" unlessotherwise specified.

Data on the properties of liquid crystal compositions are shown byT_(NI) (clearing point), η (viscosity at 20° C.), Δn (optical anisotropyat 25.0° C.), Δ.di-elect cons. (dielectric anisotropy at 25.0° C.), andV_(th) (threshold voltage at 25.0° C.), and further P (twist pitch, at25.0° C., of the composition obtained by adding 2.0 parts by weight of achiral agent (CN) expressed by formula (6) below to 100 parts by weightof the composition shown in the corresponding Example) as circumstancesrequire. ##STR36##

EXAMPLE 89 Use Example 1

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        2-HH--VVC       (No. 201)                                                                              4.0%                                                   3-HH--VVC (No. 202) 4.0%                                                      5-HH--VVC (No. 204) 4.0%                                                      2-BB--C  6.0%                                                                 2-HB--C  10.0%                                                                3-HB--C  16.0%                                                                1O1-HH-5  5.0%                                                                2-BTB-1  6.5%                                                                 1-BTB-6  13.0%                                                                4-BTB-4  6.5%                                                                 3-HHB-1  6.0%                                                                 3-HHB--O1  4.0%                                                               3-HHB-3  9.0%                                                                 3-H2BTB-2  3.0%                                                               3-H2BTB-3  3.0%                                                             ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =78.0 (°C.)

η=16.2 (mPa.s)

Δn=0.158

Δ.di-elect cons.=7.0

V_(th) =1.91 (V)

k3/k1=1.3

k3/k2=2.7

EXAMPLE 90 Use Example 2

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        1-BHH--VC         (No. 20) 9.0%                                                 2-HH--VC (No. 1) 4.0%                                                         3-HH--VC (No. 2) 4.0%                                                         4-HH--VC (No. 3) 3.0%                                                         5-HH--VC (No. 4) 3.0%                                                         1V2-BEB(F,F)--C  5.0%                                                         3-HB--C  25.0%                                                                1-BTB-3  5.0%                                                                 2-BTB-1  10.0%                                                                3-HH-4  11.0%                                                                 3-HHB-1  11.0%                                                                3-H2BTB-4  4.0%                                                               3-HB(F)TG-3  6.0%                                                           ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =98.9 (°C.)

η=28.5 (mPa.s)

Δn=0.148

Δ.di-elect cons.=7.8

V_(th) =2.15 (V)

EXAMPLE 91 Use Example 3

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        1-BHH--VCF      (No. 421)                                                                              5.0%                                                   3-BHH--VCF (No. 422) 5.0%                                                     1-BHH--VC (No. 20) 4.0%                                                       V2-HB--C  12.0%                                                               1V2-HB--C  12.0%                                                              3-HB--C  24.0%                                                                3-HB(F)--C  5.0%                                                              2-BTB-1  2.0%                                                                 3-HH-4  8.0%                                                                  3-HH--VFF  6.0%                                                               2-HHB--C  3.0%                                                                3-HHB--C  6.0%                                                                3-HB(F)TB-2  8.0%                                                           ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =95.1 (°C.)

η=24.7 (mPa.s)

Δn=0.140

Δ.di-elect cons.=9.5

V_(th) =1.81 (V)

EXAMPLE 92 Use Example 4

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        3-HH--VC          (No. 2)  15.0%                                                3-HH--VCF (No. 402) 8.0%                                                      2O1-BEB(F)--C  5.0%                                                           3O1-BEB(F)--C  15.0%                                                          4O1-BEB(F)--C  13.0%                                                          5O1-BEB--(F)--C  13.0%                                                        3-HHB(F)--C  15.0%                                                            3-HB(F)TB-4  4.0%                                                             3-HHB-1  8.0%                                                                 3-HHB--O1  4.0%                                                             ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =89.3 (°C.)

η=83.5 (mPa.s)

Δn=0.135

Δ.di-elect cons.=29.3

V_(th) =0.97 (V)

EXAMPLE 93 Use Example 5

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        3-HH--VC         (No. 2)      6.0%                                              5-HH--VC (No. 4) 8.0%                                                         5-PyB--F  4.0$                                                                3-PyB(F)--F  4.0%                                                             2-BB--C  5.0%                                                                 4-BB--C  4.0%                                                                 5-BB--C  5.0%                                                                 2-PyB-2  2.0%                                                                 3-PyB-2  2.0%                                                                 4-PyB-2  2.0%                                                                 6-PyB--O5  3.0%                                                               6-PyB--O6  3.0%                                                               6-PyB--O7  3.0%                                                               6-PyB--O8  3.0%                                                               3-PyBB--F  6.0%                                                               4-PyBB--F  6.0%                                                               5-PyBB--F  6.0%                                                               2-H2BTB-2  4.0%                                                               2-H2BTB-3  4.0%                                                               2-H2BTB-4  5.0%                                                               3-H2BTB-2  5.0%                                                               3-H2BTB-3  5.0%                                                               3-H2BTB-4  5.0%                                                             ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =95.7 (°C.)

η=40.7 (mPa.s)

Δn=0.201

Δ.di-elect cons.=6.7

V_(th) =2.24 (V)

EXAMPLE 94 Use Example 6

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        3-HH--VC        (No. 2)  10.0%                                                  3-HH--VCF (No. 402) 6.0%                                                      4-DB--C  10.0%                                                                2-BEB--C  12.0%                                                               3-BEB--C  4.0%                                                                3-PyB(F)--F  6.0%                                                             3-HEB--O4  8.0%                                                               4-HEB--O2  6.0%                                                               5-HEB--O1  6.0%                                                               3-HEB--O2  5.0%                                                               5-HEB--O2  4.0%                                                               5-HEB-5  5.0%                                                                 4-HEB-5  5.0%                                                                 1O-BEB-2  4.0%                                                                3-HHEBB--C  3.0%                                                              3-HBEBB--C  3.0%                                                              5-HBEBB--C  3.0%                                                            ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =79.0 (°C.)

η=41.8 (mPa.s)

Δn=0.121

Δ.di-elect cons.=9.5

V_(th) =1.42 (V)

EXAMPLE 95 Use Example 7

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        3-HH--VCF       (No. 402)                                                                              9.0%                                                   5-HH--VCF (No. 404) 9.0%                                                      1-BHH--VCF (No. 421) 7.0%                                                     5-HB--C  3.0%                                                                 1O1-HB--C  10.0%                                                              3-HB(F)--C  10.0%                                                             2-PyB-2  2.0%                                                                 3-PyB-2  2.0%                                                                 4-PyB-2  2.0%                                                                 1O1-HH-3  7.0%                                                                2-BTB--O1  7.0%                                                               3-HHB--F  4.0%                                                                3-HHB--O1  4.0%                                                               3-HHB-3  8.0%                                                                 3-H2BTB-2  3.0%                                                               3-H2BTB-3  3.0%                                                               2-PyBH-3  4.0%                                                                3-PyBH-3  3.0%                                                                3-PyBB-2  3.0%                                                              ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =91.5 (°C.)

η=22.2 (mPa.s)

Δn=0.139

Δ.di-elect cons.=6.0

V_(th) =1.98 (V)

EXAMPLE 96 Use Example 8

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        3-HH--VVC         (No. 202)                                                                              5.0%                                                 3-H2H--VC (No. 7) 9.0%                                                        1-BHH--VVC (No. 221) 5.0%                                                     5-BH--CV (No. 13) 3.0%                                                        3O1-BEB(F)--C  12.0%                                                          5O1-BEB(F)--C  4.0%                                                           1V2-BEB(F,F)--C  10.0%                                                        3-HH-EMe  10.0%                                                               3-HB--O2  18.0%                                                               3-HHEB--F  3.0%                                                               5-HHEB--F  3.0%                                                               3-HBEB--F  4.0%                                                               2O1-HBEB(F)--C  2.0%                                                          3-HB(F)EB(F)--C  2.0%                                                         3-HBEB(F,F)--C  2.0%                                                          3-HHB--F  4.0%                                                                3-HHB--O1  4.0%                                                               3-HEBEB--F  2.0%                                                              3-HeBEB-1  2.0%                                                             ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =90.3 (°C.)

η=41.9 (mPa.s)

Δn=0.122

Δ.di-elect cons.=22.7

V_(th) =1.12 (V)

EXAMPLE 97 Use Example 9

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        3-HH--VC          (No. 2) 8.0%                                                  5-HH--VC (No. 4) 4.0%                                                         2O1-BEB(F)--C  5.0%                                                           3O1-BEB(F)--C  12.0%                                                          5O1-BEB(F)--C  4.0%                                                           1V2-BEB(F,F)--C  16.0%                                                        3-HB--O2  10.0%                                                               3-HH-4  3.0%                                                                  3-HHB--F  3.0%                                                                3-HBEB--F  4.0%                                                               3-HHEB--F  7.0%                                                               5-HHEB--F  7.0%                                                               3-H2BTB-2  4.0%                                                               3-H2BTB-3  4.0%                                                               3-H2BTB-4  4.0%                                                               3-HB(F)TB-2  5.0%                                                           ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =88.6 (°C.)

η=44.2 (mPa.s)

Δn=0.142

Δ.di-elect cons.=28.3

V_(th) =1.01 (V)

EXAMPLE 98 Use Example 10

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        1-BHH--VC       (No. 20) 7.0%                                                   1-BHH--VCF (No. 421) 4.0%                                                     2-BEB--C  12.0%                                                               3-BEB--C  4.0%                                                                4-BEB--C  6.0%                                                                3-HB--C  28.0%                                                                3-HEB--O4  12.0%                                                              4-HEB--O2  8.0%                                                               5-HEB--O1  8.0%                                                               3-HEB--O2  6.0%                                                               5-HEB--O2  5.0%                                                             ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =68.7 (°C.)

η=33.4 (mPa.s)

Δn=0.119

Δ.di-elect cons.=10.5

V_(th) =1.39 (V)

EXAMPLE 99 Use Example 11

Liquid crystal composition comprising the following

    ______________________________________                                        3-HH--VCF       (No. 402)                                                                              4.0%                                                   3-HH--VC (No. 2) 13.0%                                                        2-BEB--C  10.0%                                                               5-BB--C  12.0%                                                                7-BB--C  7.0%                                                                 1-BTB-3  7.0%                                                                 2-BTB-1  10.0%                                                                1O--BEB-2  10.0%                                                              1O--BEB-5  12.0%                                                              3-HHB--F  4.0%                                                                3-HHB-1  7.0%                                                                 3-HHB--O1  4.0%                                                             ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =68.5 (°C.)

η=23.5 (mPa.s)

Δn=0.159

Δ.di-elect cons.=6.7

V_(th) =1.80 (V)

EXAMPLE 100 Use Example 12

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        3-HH--VC                  15.0%                                                 1V2-BEB(F,F)--C (No. 2) 8.0%                                                  3-HB--C  18.0%                                                                3-HB--O2  4.0%                                                                3-HH-4  11.0%                                                                 3-HH-5  5.0%                                                                  5-HH-2  5.0%                                                                  3-HHB-1  11.0%                                                                3-HB(F)TB-2  5.0%                                                             3-HB(F)TB-3  5.0%                                                             3-H2BTB-2  5.0%                                                               3-H2BTB-3  4.0%                                                               3-H2BTB-4  4.0%                                                             ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =101.8 (°C.)

η=16.2 (mPa.s)

Δn=0.132

Δ.di-elect cons.=8.9

V_(th) =2.08 (V)

P=11.6 (μm)

EXAMPLE 101 Use Example 13

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        3-HH--VC          (No. 2) 20.0%                                                 1V2-BEB(F,F)--C  9.0%                                                         3-HB--C  6.0%                                                                 5-HH--VFF  30.0%                                                              3-HH-4  7.0%                                                                  2-BTB-1  2.0%                                                                 3-HB(F)TB-2  5.0%                                                             3-HB(F)TB-3  5.0%                                                             3-HB(F)TB-4  4.0%                                                             3-H2BTB-2  4.0%                                                               3-H2BTB-3  4.0%                                                               3-H2BTB-4  4.0%                                                             ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =101.0 (°C.)

η=14.5 (mPa.s)

Δn=0.133

Δ.di-elect cons.=8.5

V_(th) =2.13 (V)

P=10.7 (μm)

EXAMPLE 102 Use Example 14

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        1-BHHVC           (No. 21) 10.0%                                                1V2-BEB(F,F)--C  8.0%                                                         3-HB--C  19.0%                                                                3-HB--O2  11.0%                                                               3-HH-4  11.0%                                                                 3-HH-5  5.0%                                                                  5-HH-2  5.0%                                                                  3-HHB-1  11.0%                                                                3-HB(F)TB-2  4.0%                                                             3-HB(F)TB-3  4.0%                                                             3-H2BTB-2  4.0%                                                               3-H2BTB-3  4.0%                                                               3-H2BTB-4  4.0%                                                             ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =100.2 (°C.)

η=17.5 (mPa.s)

Δn=0.132

Δ.di-elect cons.=8.8

V_(th) =2.14 (V)

P=11.8 (μm)

EXAMPLE 103 Use Example 15

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        2-HH--VVC       (No. 201)                                                                              3.0%                                                   3-HH--VVC (No. 202) 3.0%                                                      5-HH--VVC (No. 204) 4.0%                                                      2-HHB(F)--F  17.0%                                                            3-HHB(F)--F  17.0%                                                            5-HHB(F)--F  16.0%                                                            3-H2HB(F)--F  5.0%                                                            5-H2HB(F)--F  10.0%                                                           2-HBB(F)--F  6.0%                                                             3-HBB(F)--F  6.0%                                                             5-HBB(F)--F  13.0%                                                          ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =109.7 (°C.)

η=27.5 (mPa.s)

Δn=0.104

Δ.di-elect cons.=5.6

V_(th) =2.12 (V)

EXAMPLE 104 Use Example 16

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        5-BH--VC        (No. 13) 5.0%                                                   7-HB(F)--F  5.0%                                                              5-H2B(F)--F  5.0%                                                             3-HB--O2  10.0%                                                               3-HH-4  5.0%                                                                  2-HHB(F)--F  5.0%                                                             3-HHB(F)--F  10.0%                                                            5-HHB(F)--F  10.0%                                                            3-H2HB(F)--F  5.0%                                                            2-HBB(F)--F  3.0%                                                             3-HBB(F)--F  3.0%                                                             5-HBB(F)--F  6.0%                                                             2-H2BB(F)--F  5.0%                                                            3-H2BB(F)--F  6.0%                                                            3-HHB-1  8.0%                                                                 3-HHB--O1  5.0%                                                               3-HHB-3  4.0%                                                               ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =86.0 (°C.)

η=19.1 (mPa.s)

Δn=0.096

Δ.di-elect cons.=3.5

V_(th) =2.69 (V)

EXAMPLE 105 Use Example 17

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        C--BH--VC        (No. 801)                                                                              3.0%                                                  7-HB(F,F)--F  3.0%                                                            3-HB--O2  7.0%                                                                2-HHB(F)--F  10.0%                                                            3-HHB(F)--F  10.0%                                                            5-HHB(F)--F  10.0%                                                            2-HBB(F)--F  9.0%                                                             3-HBB(F)--F  9.0%                                                             5-HBB(F)--F  16.0%                                                            2-HBB--F  4.0%                                                                3-HBB--F  4.0%                                                                3-HBB(F,F)--F  5.0%                                                           5-HBB(F,F)--F  10.0%                                                        ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =86.4 (°C.)

η=27.9 (mPa.s)

Δn=0.118

Δ.di-elect cons.=11.9

V_(th) =1.79 (V)

EXAMPLE 106 Use Example 18

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        1-BBH--VCF       (No. 420)                                                                              5.0%                                                  7-HB(F,F)--F  4.0%                                                            3-H2HB(F,F)--F  12.0%                                                         4-H2HB(F,F)--F  10.0%                                                         5-H2HB(F,F)--F  10.0%                                                         3-HHB(F,F)--F  10.0%                                                          3-HH2B(F,F)--F  15.0%                                                         5-HH2B(F,F)--F  10.0%                                                         3-HBB(F,F)--F  12.0%                                                          5-HBB(F,F)--F  12.0%                                                        ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =79.8 (°C.)

η=29.6 (mPa.s)

Δn=0.094

Δ.di-elect cons.=8.7

V_(th) =1.60 (V)

EXAMPLE 107 Use Example 19

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        3-HH-2VC         (No. 102)                                                                              5.0%                                                  3-HB--CL  10.0%                                                               5-HB--CL  4.0%                                                                7-HB--CL  4.0%                                                                1O1-HH-5  5.0%                                                                2-HBB(F)--F  3.0%                                                             3-HBB(F)--F  8.0%                                                             5-HBB(F)--F  14.0%                                                            4-HHB--CL  8.0%                                                               5-HHB--CL  8.0%                                                               3-H2HB(F)--CL  4.0%                                                           3-HBB(F,F)--F  10.0%                                                          5-H2BB(F,F)--F  9.0%                                                          3-HB(F)VB-2  4.0%                                                             3-HB(F)VB-3  4.0%                                                           ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =92.9 (°C.)

η=21.6 (mPa.s)

Δn=0.131

Δ.di-elect cons.=5.0

V_(th) =2.34 (V)

EXAMPLE 108 Use Example 20

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        3-H2H--VC         (No. 7) 8.0%                                                  3-HHB(F,F)--F  9.0%                                                           4-H2HB(F,F)--F  8.0%                                                          5-H2HB(F,F)--F  8.0%                                                          3-HBB(F,F)--F  21.0%                                                          5-HBB(F,F)--F  20.0%                                                          3-H2BB(F,F)--F  10.0%                                                         5-HHBB(F,F)--F  3.0%                                                          3-HH2BB(F,F)--F  3.0%                                                         5-HHEBB--F  2.0%                                                              1O1-HBBH-4  4.0%                                                              1O1-HBBH-5  4.0%                                                            ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =102.6 (°C.)

η=35.8 (mPa.s)

Δn=0.119

Δ.di-elect cons.=8.6

V_(th) =1.87 (V)

EXAMPLE 109 Use Example 21

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        2-HH--VC           (No. 1) 5.0%                                                 3-HH--VC (No. 2) 5.0%                                                         5-HB--F  12.0%                                                                6-HB--F  9.0%                                                                 7-HB--F  7.0%                                                                 2-HHB--OCF3  7.0%                                                             3-HHB--OCF3  11.0%                                                            4-HHB--OCF3  7.0%                                                             5-HHB--OCF3  5.0%                                                             3-HH2B--OCF3  4.0%                                                            5-HH2B--OCF3  4.0%                                                            3-HHB(F,F)--OCF3  5.0%                                                        3-HBB(F)--F  10.0%                                                            3-HH2B(F)--F  3.0%                                                            3-HB(F)BH-3  3.0%                                                             5-HBBH-3  3.0%                                                              ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =90.9 (°C.)

η=13.7 (mPa.s)

Δn=0.089

Δ.di-elect cons.=4.6

V_(th) =2.42 (V)

EXAMPLE 110 Use Example 22

Liquid crystal composition comprising the following compounds in thefollowing content was prepared:

    ______________________________________                                        3-HH--VCF         (No. 402)                                                                              5.0%                                                 5-HH--VCF (No. 404) 5.0%                                                      5-H4HB(F,F)--F  7.0%                                                          5-H4HB--OCF3  15.0%                                                           3-H4HB(F,F)--CF3  8.0%                                                        5-H4HB(F,F)--CF3  10.0%                                                       3-HB--CL  6.0%                                                                5-HB--CL  4.0%                                                                4-H2BB(F)--F  5.0%                                                            5-HVHB(F,F)--F  5.0%                                                          3-HHB--OCF3  5.0%                                                             3-H2HB--OCF3  5.0%                                                            V-HHB(F)--F  5.0%                                                             3-HChB(F)--F  5.0%                                                            5-HHEB--OCF3  2.0%                                                            3-HBEB(F,F)--F  5.0%                                                          5-HH--V2F  3.0%                                                             ______________________________________                                    

Properties of this composition were determined and the results were asfollows:

T_(NI) =72.1 (°C.)

η=23.5 (mPa.s)

Δn=0.085

Δ.di-elect cons.=7.7

V_(th) =1.84 (V)

INDUSTRIAL APPLICABILITY

According to the present invention, novel liquid crystalline compoundswhich can impart a large elastic constant ratio to liquid crystalcompositions while maintaining excellent characteristics as liquidcrystal component, that is, a wide temperature range of liquid crystal,excellent miscibility with other liquid crystals, and a low viscosity;liquid crystal compositions comprising the liquid crystalline compounds;and liquid crystal display devices comprising the composition can beprovided.

We claim:
 1. An acrylonitrile derivative expressed by general formula I##STR37## wherein ring A¹, ring A², and Ring A³ independently represent1,4-phenylene one or two hydrogen atoms of which may be replaced byfluorine atom, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, or1,3-pyrimidine-2,5-diyl, R¹ represents cyano group, halogen atom, analkyl group, an alkoxy group, an alkyl group one or more hydrogen atomsof which are replaced by fluorine atom, an alkoxy group one or morehydrogen atoms of which are replaced by fluorine atom, or an alkoxyalkylgroup when the ring A¹ represents 1,4-phenylene, but when the ring A¹represents 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, or1,3-pyrimidine-2,5-diyl, R¹ represents an alkyl group, an alkoxy group,or an alkoxyalkyl group, B¹, B², and B³ represent a covalent bond,ethylene, ethenylene, ethynylene, oxymethylene, carbonyloxy,1,4-butanediyl, or 1,4-butenediyl, n1, n2, and n3 are independently 0 or1, R² represents a group expressed by formula II or formula III##STR38## wherein X represents hydrogen atom or fluorine atom, and ringH represents 1,4-cyclohexylene, provided that in no case two or morehetero-rings are included in a molecule at the same time.
 2. Theacrylonitrile derivative according to claim 1 wherein n1 and n2 are 0.3. The acrylonitrile derivative according to claim 1 wherein n1 is 0 andn2 is
 1. 4. The acrylonitrile derivative according to claim 1 wherein n1and n2 are
 1. 5. The acrylonitrile derivative according to claim 1wherein R¹ is an alkyl group, an alkoxy group, or an alkoxyalkyl group,ring A¹, ring A², and ring A³ represent 1,4-phenylene one or twohydrogen atoms of which may be replaced by fluorine atom, or1,4-cyclohexylene.
 6. The acrylonitrile derivative according to claim 2wherein R¹ represents an alkyl group, an alkoxy group, or an alkoxyalkylgroup, and ring A1 represents 1,4-phenylene or 1,4-cyclohexylene.
 7. Theacrylonitrile derivative according to claim 5 wherein either n1 or n2 is0, and both B² and B³ represent a covalent bond.
 8. The acrylonitrilederivative according to claim 5 wherein either n1 or n2 is 0, B² and B³independently represent a covalent bond or 1,2-ethylene, and R²represents a group expressed by the formula II.
 9. The acrylonitrilederivative according to claim 5 wherein either n1 or n2 is 0, B² and B³independently represent a covalent bond or 1,2-ethylene, and R²represents a group expressed by the formula III.
 10. The acrylonitrilederivative according to claim 1 wherein ring A¹ represents 1,4-phenyleneone or two hydrogen atoms of which may be replaced by fluorine atom, andR¹ represents cyano group, halogen atom, an alkyl group one or morehydrogen atoms of which are replaced by fluorine atom, or an alkoxygroup one or more hydrogen atoms of which are replaced by fluorine atom.11. The acrylonitrile derivative according to claim 2 wherein ring A¹represents 1,4-phenylene one or more hydrogen atoms of which may bereplaced by fluorine atom, and R¹ represents cyano group, halogen atom,an alkyl group one or more hydrogen atoms of which are replaced byfluorine atom, or an alkoxy group one or more hydrogen atoms of whichare replaced by fluorine atom.
 12. The acrylonitrile derivativeaccording to claim 3 wherein ring A¹ represents 1,4-phenylene one ormore hydrogen atoms of which may be replaced by fluorine atom, and R¹represents cyano group, halogen atom, an alkyl group one or morehydrogen atoms of which are replaced by fluorine atom, or an alkoxygroup one or more hydrogen atoms of which are replaced by fluorine atom.13. The acrylonitrile derivative according to claim 10 wherein R¹represents cyano group or halogen atom.
 14. The acrylonitrile derivativeaccording to claim 10 wherein either n1 or n2 is 0, and both B² and B³represent a covalent bond.
 15. The acrylonitrile derivative according toclaim 13 wherein either n1 or n2 is 0, B² and B³ represent a covalentbond, and R² represents a group expressed by the formula II.
 16. Theacrylonitrile derivative according to claim 13 wherein either n1 or n2is 0, both B² and B³ represent a covalent bond, and R2 represents agroup expressed by the formula III.
 17. A liquid crystal compositioncomprising two or more components at least one of which is a liquidcrystalline compound expressed by the general formula I defined inclaim
 1. 18. A liquid crystal composition comprising, as a firstcomponent, at least one acrylonitrile derivative defined in any one ofclaims 1 to 16, and comprising, as a second component, at least onecompound selected from the group consisting of the compounds expressedby any one of general formulas IV, V, and VI ##STR39## wherein R³represents an alkyl group having 1 to 10 carbon atoms, Y representsfluorine atom or chlorine atom, Q¹ and Q² independently representhydrogen atom or fluorine atom, m is 1 or 2, and Z¹ and Z² independentlyrepresent --CH₂ CH₂ -- or a covalent bond.
 19. A liquid crystalcomposition comprising, as a first component, at least one acrylonitrilederivative defined in any one of claims 1 to 16, and comprising, as asecond component, at least one compound selected from the groupconsisting of the compounds expressed by any one of general formula VII,VIII, IX, X, and XI ##STR40## wherein R⁴ represents an alkyl grouphaving 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbonatoms, any methylene group (--CH₂ --) in each of the alkyl group andalkenyl group may be replaced by oxygen atom (--O--), but in no case twoor more methylene groups are continuously replaced by oxygen group, Z³represents --CH₂ CH₂ --, --COO--, or a covalent bond, Q³ representshydrogen atom or fluorine atom, ring C represents 1,4-cyclohexylene,1,4-phenylene, or 1,3-dioxane-2,5-diyl, and Q is 0 or 1, ##STR41##wherein R⁵ represents an alkyl group having 1 to 10 carbon atoms, Q⁴represents hydrogen atom or fluorine atom, and o is 0 or 1, ##STR42##wherein R⁶ represents an alkyl group having 1 to 10 carbon atoms, ring Drepresents 1,4-cyclohexylene or 1,4-phenylene, Q⁵ and Q⁶ representhydrogen atom or fluorine atom, respectively, Z⁴ represents --COO-- or acovalent bond, and p is 0 or 1, ##STR43## wherein R⁷ and R⁸independently represent an alkyl group having 1 to 10 carbon atoms or analkenyl group having 2 to 10 carbon atoms, any methylene group (--CH₂--) in each of the alkyl group and alkenyl group may be replaced byoxygen atom, but in no case two or more methylene groups arecontinuously replaced by oxygen atom, ring E represents1,4-cyclohexylene, 1,3-pyrimidine-2,5-diyl, or 1,4-phenylene, ring Frepresents 1,4-cyclohexylene or 1,4-phenylene, and Z⁵ represents--C.tbd.C--, --COO--, --CH₂ CH₂ --, or a covalent bond ##STR44## whereinR⁹ represents an an alkyl group or an alkoxy group having 1 to 10 carbonatoms, R¹⁰ represents an alkyl, an alkoxy, or an alkoxymethyl grouphaving 1 to 10 carbon atoms, ring G represents 1,4-cyclohexylene or1,3-pyrimidine-2,5-diyl, ring I and ring J independently represent1,4-cyclohexylene or 1,4-phenylene, Z⁶ represents --COO--, --CH₂ CH₂ --,or a covalent bond, Z⁷ represents--C.tbd.C--, --COO--, or a covalentbond, and Q⁷ represents hydrogen atom or fluorine atom.
 20. A liquidcrystal display device comprising a liquid crystal composition definedin claim
 17. 21. A liquid crystal display device comprising a liquidcrystal composition defined in claim
 18. 22. A liquid crystal displaydevice comprising a liquid crystal composition defined in claim
 19. 23.A liquid crystal composition comprising, as a first component, at leastone liquid crystalline compound defined in any one of claims 1 to 16,comprising, as a part of a second component, at least one compoundselected from the group consisting of the compounds expressed by any oneof the general formulas IV, V, and VI, and comprising, as another partof the second component, at least one compound selected from the groupconsisting of the compounds expressed by any one of the general formulasVII, VIII, IX, X, and XI ##STR45## wherein R³ represents an alkyl grouphaving 1 to 10 carbon atoms, Y represents fluorine atom or chlorineatom, Q¹ and Q² independently represent hydrogen atom or fluorine atom,m is 1 or 2, and Z¹ and Z² independently represent --CH₂ CH₂ -- or acovalent bond, ##STR46## wherein R⁴ represents an alkyl group having 1to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, anymethylene group (--CH₂ --) in each of the alkyl group and alkenyl groupmay be replaced by oxygen atom (--O--), but in no case two or moremethylene groups are continuously replaced by oxygen group, Z³represents --CH₂ CH₂ --, --COO--, or a covalent bond, Q³ representshydrogen atom or fluorine atom, ring C represents 1,4-cyclohexylene,1,4-phenylene, or 1,3-dioxane-2,5-diyl, and l is 0 or 1, ##STR47##wherein R⁵ represents an alkyl group having 1 to 10 carbon atoms, Q⁴represents hydrogen atom or fluorine atom, and o is 0 or 1, ##STR48##wherein R⁶ represents an alkyl group having 1 to 10 carbon atoms, ring Drepresents 1,4-cyclohexylene or 1,4-phenylene, Q⁵ and Q⁶ representhydrogen atom or fluorine atom, respectively, Z⁴ represents --COO-- or acovalent bond, and p is 0 or 1, ##STR49## wherein R⁷ and R⁸independently represent an alkyl group having 1 to 10 carbon atoms or analkenyl group having 2 to 10 carbon atoms, any methylene group (--CH₂--) in each of the alkyl group and alkenyl group may be replaced byoxygen atom, but in no case two or more methylene groups arecontinuously replaced by oxygen atom, ring E represents1,4-cyclohexylene, 1,3-pyrimidine-2,5-diyl, or 1,4-phenylene, ring Frepresents 1,4-cyclohexylene or 1,4-phenylene, and Z⁵ represents--C.tbd.C--, --COO--, --CH₂ CH₂ --, or a covalent bond, ##STR50##wherein R⁹ represents an alkyl group or an alkoxy group having 1 to 10carbon atoms, R¹⁰ represents an alkyl, an alkoxy, or an alkoxymethylgroup having 1 to 10 carbon atoms, ring G represents 1,4-cyclohexyleneor 1,3-pyrimidine-2,5-diyl, ring I and ring J independently represent1,4-cyclohexylene or 1,4-phenylene, Z⁶ represents --COO--, CH₂ CH₂, or acovalent bond, Z⁷ represents --C.tbd.C--, --COO--, or a covalent bond,and Q⁷ represents hydrogen atom or fluorine atom.
 24. A liquid crystaldisplay device comprising a liquid crystal composition defined in claim23.